Concentrated fabric softening composition

ABSTRACT

Principal solvents, especially mono-ol and diol principal solvents, having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, and more preferably from about 0.40 to about 0.60, are disclosed that have the ability to make clear aqueous fabric softener compositions containing relatively high concentrations of fabric softener actives having highly unsaturated hydrocarbon moieties or branched chains in two long-chain hydrophobic groups with specific cis/trans ratios and having long chain hydrocarbon groups with an IV of from about 70 to about 140 for the unsaturated groups corresponding to fatty acids with the same number of carbons and the same configuration, and the said principal solvents are used at levels of less than about 40%. The fabric softener actives are preferably prepared in the presence of chelating agent and/or antioxidant, as disclosed herein. Such materials are new. Other solvents can be present. Premixes of the fabric softening actives, the principal solvents, and, optionally, other solvents are useful in the preparation of complete formulations by obviating/limiting the need for heating.

This application claims the benefit of provisional application No.60/028,904 filed Oct. 21, 1996.

TECHNICAL FIELD

The present invention relates to preferably translucent, or, morepreferably, clear, aqueous, concentrated, liquid softening compositionsuseful for softening cloth. It especially relates to textile softeningcompositions for use in the rinse cycle of a textile launderingoperation to provide excellent fabric-softening/static-control benefits,the compositions being characterized by, e.g., reduced staining offabric, excellent water dispersibility, rewettability, and/or storageand viscosity stability at sub-normal temperatures, i.e., temperaturesbelow normal room temperature, e.g., 25° C.

BACKGROUND OF THE INVENTION

Concentrated clear compositions containing ester and/or amide linkedfabric softening actives are disclosed in co-pending application Ser.No. 08/69,694, filed Jul. 11, 1996 in the names of E. H. Wahl, T. Trinh,E. P. Gosselink, J. C. Letton, and M. R. Sivik, for Fabric SofteningCompound/Composition, said application being incorporated herein byreference. The fabric softener actives in said applications are allbiodegradable ester-linked materials, containing, as long hydrophobicgroups, both unsaturated and branched chains.

SUMMARY OF THE INVENTION

The compositions herein comprise:

A. from about 2% to about 80% of fabric softener active containing atleast two C₆-C₂₂ hydrocarbyl groups, but no more than one being lessthan C₁₂ and the the other is at least C₁₆, the groups having an IV fromabout 70 to about 140, or branched; and

B. less than about 40% by weight of the composition of principal solventhaving a ClogP of from about 0.15 to about 0.64, and at least somedegree of asymmetry, said principal solvent containing insufficientamounts of solvents selected from the group consisting of:2,2,4-trimethyl-1,3-pentane diol; the ethoxylate, diethoxylate, ortriethoxylate derivatives of 2,2,4-trimethyl-1,3-pentane diol; and/or2-ethylhexyl-1,3-diol, to provide an aqueous stable composition bythemselves, said principal solvent being sufficient to make thecompositions clear.

Preferably, the compositions are aqueous, stable clear fabric softenercompositions containing:

A. from about 2% to about 80%, preferably from about 13% to about 75%,more preferably from about 17% to about 70%, and even more preferablyfrom about 19% to about 65%, by weight of the composition, of cationicfabric softener active which is selected from:

(1) softener having the formula:

R_(4−m)−N⁽⁺⁾−R¹ _(m)A⁻

 wherein each m is 2 or 3, each R¹ is a C₆-C₂₂, preferably C₁₄-C₂₀, butno more than one being less than about C₁₂ and then the other is atleast about 16, hydrocarbyl, or substituted hydrocarbyl substituent,preferably C₁₀-C₂₀ alkyl or alkenyl (unsaturated alkyl, includingpolyunsaturated alkyl, also referred to sometimes as “alkylene”), mostpreferably C₁₂-C₁₈ alkyl or alkenyl, and where the Iodine Value(hereinafter referred to as “IV”) of a fatty acid containing this R¹group is from about 70 to about 140, more preferably from about 80 toabout 130; and most preferably from about 90 to about 115 (as usedherein, the term “Iodine Value” means the Iodine Value of a “parent”fatty acid, or “corresponding” fatty acid, which is used to define alevel of unsaturation for an R¹ group that is the same as the level ofunsaturation that would be present in a fatty acid containing the sameR¹ group) with, preferably, a cis/trans ratio of from about 1:1 to about50:1, the minimum being 1:1, preferably from about 2:1 to about 40:1,more preferably from about 3:1 to about 30:1, and even more preferablyfrom about 4:1 to about 20:1; each R¹ can also preferably be a branchedchain C₁₄-C₂₂ alkyl group, preferably a branched chain C₁₆-C₁₈ group;each R is H or a short chain C₁-C₆, preferably C₁-C₃ alkyl orhydroxyalkyl group, e.g., methyl (most preferred), ethyl, propyl,hydroxyethyl, and the like, benzyl, or (R²O)₂₋₄H where each R² is a C₁₋₆alkylene group; and A⁻ is a softener compatible anion, preferably,chloride, bromide, methylsulfate, ethylsulfate, sulfate, and nitrate,more preferably chloride and methyl sulfate;

(2) softener having the formula:

 wherein each R, R¹, and A⁻ have the definitions given above; each R² isa C₁₋₆ alkylene group, preferably an ethylene group; and G is an oxygenatom or an —NR— group;

(3) softener having the formula:

 wherein R¹, R² and G are defined as above;

(4) reaction products of substantially unsaturated and/or branched chainhigher fatty acids with dialkylenetriamines in, e.g. a molecular ratioof about 2:1, said reaction products containing compounds of theformula:

R¹—C(O)—NH—R²—NH—R³—NH—C(O)—R¹

 wherein R¹, R² are defined as above, and each R³ is a C₁₋₆ alkylenegroup, preferably an ethylene group;

(5) softener having the formula:

[R¹—C(O)—NR—R²—N(R)₂—R³—NR—C(O)—R¹]⁺A⁻

 wherein R, R¹, R², R³ and A⁻ are defined as above;

(6) the reaction product of substantially unsaturated and/or branchedchain higher fatty acid with hydroxyalkylalkylenediamines in a molecularratio of about 2:1, said reaction products containing compounds of theformula:

R¹—C(O)—NH—R²—N(R³OH)—C(O)—R¹

 wherein R¹, R² and R³ are defined as above;

(7) softener having the formula:

 wherein R, R¹, R², and A⁻ are defined as above; and

(8) mixtures thereof;

B. less than about 40%, preferably from about 10% to about 35%, morepreferably from about 12% to about 25%. and even more preferably fromabout 14% to about 20%, by weight of the composition of principalsolvent having a ClogP of from about 0.15 to about 0.64, preferably fromabout 0.25 to about 0.62, and more preferably from about 0.40 to about0.60, said principal solvent containing insufficient amounts of solventsselected from the group consisting of: 2,2,4-trimethyl-1,3-pentanediol;the ethoxylate, diethoxylate, or triethoxylate derivatives of2,2,4-trimethyl-1,3-pentanediol; and/or 2-ethyl-1,3-hexanediol, and/ormixtures thereof, when used by themselves, to provide a clear product,preferably insufficient to provide a stable product, more preferablyinsufficient to provide a detectable change in the physicalcharacteristics of the composition, and especially completely freethereof, and the principal solvent preferably being selected from thegroup consisting of:

I. mono-ols including:

a. n-propanol; and/or

b. 2-butanol and/or 2-methyl-2-propanol;

II. hexane diol isomers including: 2,3-butanediol, 2,3-dimethyl-;1,2-butanediol, 2,3-dimethyl-; 1,2-butanediol, 3,3-dimethyl-;2,3-pentanediol, 2-methyl-; 2,3-pentanediol, 3-methyl-; 2,3-pentanediol,4-methyl-; 2,3-hexanediol; 3,4-hexanediol; 1,2-butanediol, 2-ethyl-;1,2-pentanediol, 2-methyl-; 1,2-pentanediol, 3-methyl-; 1,2-pentanediol,4-methyl-; and/or 1,2-hexanediol;

III. heptane diol isomers including: 1,3-propanediol, 2-butyl-;1,3-propanediol, 2,2-diethyl-; 1,3-propanediol, 2-(1-methylpropyl)-;1,3-propanediol, 2-(2-methylpropyl)-; 1,3-propanediol,2-methyl-2-propyl-; 1,2-butanediol, 2,3,3-trimethyl-; 1,4-butanediol,2-ethyl-2-methyl-; 1,4-butanediol, 2-ethyl-3-methyl-; 1,4-butanediol,2-propyl-; 1,4-butanediol, 2-isopropyl-; 1,5-pentanediol, 2,2-dimethyl-;1,5-pentanediol, 2,3-dimethyl-; 1,5-pentanediol, 2,4-dimethyl-;1,5-pentanediol, 3,3-dimethyl-; 2,3-pentanediol, 2,3-dimethyl-;2,3-pentanediol, 2,4-dimethyl-; 2,3-pentanediol, 3,4-dimethyl-;2,3-pentanediol, 4,4-dimethyl-; 3,4-pentanediol, 2,3-dimethyl-;1,5-pentanediol, 2-ethyl-; 1,6-hexanediol, 2-methyl-; 1,6-hexanediol,3-methyl-; 2,3-hexanediol, 2-methyl-; 2,3-hexanediol, 3-methyl-;2,3-hexanediol, 4-methyl-; 2,3-hexanediol, 5-methyl-; 3,4-hexanediol,2-methyl-; 3,4-hexanediol, 3-methyl-; 1,3-heptanediol; 1,4-heptanediol;1,5-heptanediol; and/or 1,6-heptanediol;

IV. octane diol isomers including: 1,3-propanediol, 2-(2-methylbutyl)-;1,3-propanediol, 2-(1,1-dimethylpropyl)-1,3-propanediol,2-(1,2-dimethylpropyl)-; 1,3-propanediol, 2-(1-ethylpropyl)-;1,3-propanediol, 2-(1-methylbutyl)-; 1,3-propanediol,2-(2,2-dimethylpropyl)-; 1,3-propanediol, 2-(3-methylbutyl)-;1,3-propanediol, 2-butyl-2-methyl-; 1,3-propanediol,2-ethyl-2-isopropyl-; 1,3-propanediol, 2-ethyl-2-propyl-;1,3-propanediol, 2-methyl-2-(1-methylpropyl)-; 1,3-propanediol,2-methyl-2-(2-methylpropyl)-; 1,3-propanediol,2-tertiary-butyl-2-methyl-; 1,3-butanediol, 2,2-diethyl-;1,3-butanediol, 2-(1-methylpropyl)-; 1,3-butanediol, 2-butyl-;1,3-butanediol, 2-ethyl-2,3-dimethyl-; 1,3-butanediol,2-(1,1-dimethylethyl)-; 1,3-butanediol, 2-(2-methylpropyl)-;1,3-butanediol, 2-methyl-2-isopropyl-; 1,3-butanediol,2-methyl-2-propyl-; 1,3-butanediol, 3-methyl-2-isopropyl-;1,3-butanediol, 3-methyl-2-propyl-; 1,4-butanediol, 2,2-diethyl-;1,4-butanediol, 2-methyl-2-propyl-; 1,4-butanediol, 2-(1-methylpropyl)-;1,4-butanediol, 2-ethyl-2,3-dimethyl-; 1,4-butanediol,2-ethyl-3,3-dimethyl-; 1,4-butanediol, 2-(1,1-dimethylethyl)-;1,4-butanediol, 2-(2-methylpropyl)-; 1,4-butanediol, 2-methyl-3-propyl-;1,4-butanediol, 3-methyl-2-isopropyl-; 1,3-pentanediol,2,2,3-trimethyl-; 1,3-pentanediol, 2,2,4-trimethyl-; 1,3-pentanediol,2,3,4-trimethyl-; 1,3-pentanediol, 2,4,4-trimethyl-; 1,3-pentanediol,3,4,4-trimethyl-; 1,4-pentanediol, 2,2,3-trimethyl-; 1,4-pentanediol,2,2,4-trimethyl-; 1,4-pentanediol, 2,3,3-trimethyl-; 1,4-pentanediol,2,3,4-trimethyl-; 1,4-pentanediol, 3,3,4-trimethyl-; 1,5-pentanediol,2,2,3-trimethyl-; 1,5-pentanediol, 2,2,4-trimethyl-; 1,5-pentanediol,2,3,3-trimethyl-; 1,5-pentanediol, 2,3,4-trimethyl-; 2,4-pentanediol,2,3,3-trimethyl-; 2,4-pentanediol, 2,3,4-trimethyl-; 1,3-pentanediol,2-ethyl-2-methyl-; 1,3-pentanediol, 2-ethyl-3-methyl-; 1,3-pentanediol,2-ethyl-4-methyl-; 1,3-pentanediol, 3-ethyl-2-methyl-; 1,4-pentanediol,2-ethyl-2-methyl-; 1,4-pentanediol, 2-ethyl-3-methyl-; 1,4-pentanediol,2-ethyl-4-methyl-; 1,4-pentanediol, 3-ethyl-2-methyl-; 1,4-pentanediol,3-ethyl-3-methyl-; 1,5-pentanediol, 2-ethyl-2-methyl-; 1,5-pentanediol,2-ethyl-3-methyl-; 1,5-pentanediol, 2-ethyl-4-methyl-; 1,5-pentanediol,3-ethyl-3-methyl-; 2,4-pentanediol, 3-ethyl-2-methyl-; 1,3-pentanediol,2-isopropyl-; 1,3-pentanediol, 2-propyl-; 1,4-pentanediol, 2-isopropyl-;1,4-pentanediol, 2-propyl-; 1,4-pentanediol, 3-isopropyl-;1,5-pentanediol, 2-isopropyl-; 2,4-pentanediol, 3-propyl-;1,3-hexanediol, 2,2-dimethyl-; 1,3-hexanediol, 2,3-dimethyl-;1,3-hexanediol, 2,4-dimethyl-; 1,3-hexanediol, 2,5-dimethyl-;1,3-hexanediol, 3,4-dimethyl-; 1,3-hexanediol, 3,5-dimethyl-;1,3-hexanediol, 4,5-dimethyl-; 1,4-hexanediol, 2,2-dimethyl-;1,4-hexanediol, 2,3-dimethyl-; 1,4-hexanediol, 2,4-dimethyl-;1,4-hexanediol, 2,5-dimethyl-; 1,4-hexanediol, 3,3-dimethyl-;1,4-hexanediol, 3,4-dimethyl-; 1,4-hexanediol, 3,5-dimethyl-;1,3-hexanediol, 4,4-dimethyl-; 1,4-hexanediol, 4,5-dimethyl-;1,4-hexanediol, 5,5-dimethyl-; 1,5-hexanediol, 2,2-dimethyl-;1,5-hexanediol, 2,3-dimethyl-; 1,5-hexanediol, 2,4-dimethyl-;1,5-hexanediol, 2,5-dimethyl-; 1,5-hexanediol, 3,3-dimethyl-;1,5-hexanediol, 3,4-dimethyl-; 1,5-hexanediol, 3,5-dimethyl-;1,5-hexanediol, 4,5-dimethyl-; 1,6-hexanediol, 2,2-dimethyl-;1,6-hexanediol, 2,3-dimethyl-; 1,6-hexanediol, 2,4-dimethyl-;1,6-hexanediol, 2,5-dimethyl-; 1,6-hexanediol, 3,3-dimethyl-;1,6-hexanediol, 3,4-dimethyl-; 2,4-hexanediol, 2,3-dimethyl-;2,4-hexanediol, 2,4-dimethyl-; 2,4-hexanediol, 2,5-dimethyl-;2,4-hexanediol, 3,3-dimethyl-; 2,4-hexanediol, 3,4-dimethyl-;2,4-hexanediol, 3,5-dimethyl-; 2,4-hexanediol, 4,5-dimethyl-;2,4-hexanediol, 5,5-dimethyl-; 2,5-hexanediol, 2,3-dimethyl-;2,5-hexanediol, 2,4-dimethyl-; 2,5-hexanediol, 2,5-dimethyl-;2,5-hexanediol, 3,3-dimethyl-; 2,5-hexanediol, 3,4-dimethyl-;2,6-hexanediol, 3,3-dimethyl-; 1,3-hexanediol, 2-ethyl-; 1,3-hexanediol,4-ethyl-; 1,4-hexanediol, 2-ethyl-; 1,4-hexanediol, 4-ethyl-;1,5-hexanediol, 2-ethyl-; 2,4-hexanediol, 3-ethyl-; 2,4-hexanediol,4-ethyl-; 2,5-hexanediol, 3-ethyl-; 1,3-heptanediol, 2-methyl-;1,3-heptanediol, 3-methyl-; 1,3-heptanediol, 4-methyl-; 1,3-heptanediol,5-methyl-; 1,3-heptanediol, 6-methyl-; 1,4-heptanediol, 2-methyl-;1,4-heptanediol, 3-methyl-; 1,4-heptanediol, 4-methyl-; 1,4-heptanediol,5-methyl-; 1,4-heptanediol, 6-methyl-; 1,5-heptanediol, 2-methyl-;1,5-heptanediol, 3-methyl-; 1,5-heptanediol, 4-methyl-; 1,5-heptanediol,5-methyl-; 1,5-heptanediol, 6-methyl-; 1,6-heptanediol, 2-methyl-;1,6-heptanediol, 3-methyl-; 1,6-heptanediol, 4-methyl-; 1,6-heptanediol,5-methyl-; 1,6-heptanediol, 6-methyl-; 2,4-heptanediol, 2-methyl-;2,4-heptanediol, 3-methyl-; 2,4-heptanediol, 4-methyl-; 2,4-heptanediol,5-methyl-; 2,4-heptanediol, 6-methyl-; 2,5-heptanediol, 2-methyl-;2,5-heptanediol, 3-methyl-; 2,5-heptanediol, 4-methyl-; 2,5-heptanediol,5-methyl-; 2,5-heptanediol, 6-methyl-; 2,6-heptanediol, 2-methyl-;2,6-heptanediol, 3-methyl-; 2,6-heptanediol, 4-methyl-; 3,4-heptanediol,3-methyl-; 3,5-heptanediol, 2-methyl-; 3,5-heptanediol, 3-methyl-;3,5-heptanediol, 4-methyl-; 2,4-octanediol; 2,5-octanediol;2,6-octanediol; 2,7-octanediol; 3,5-octanediol; and/or 3,6-octanediol;

V. nonane diol isomers including: 2,4-pentanediol, 2,3,3,4-tetramethyl-;2,4-pentanediol, 3-tertiarybutyl-; 2,4-hexanediol, 2,5,5-trimethyl-;2,4-hexanediol, 3,3,4-trimethyl-; 2,4-hexanediol, 3,3,5-trimethyl-;2,4-hexanediol, 3,5,5-trimethyl-; 2,4-hexanediol, 4,5,5-trimethyl-;2,5-hexanediol, 3,3,4-trimethyl-; and/or 2,5-hexanediol,3,3,5-trimethyl-;

VI. glyceryl ethers and/or di(hydroxyalkyl)ethers including:1,2-propanediol, 3-(n-pentyloxy)-; 1,2-propanediol, 3-(2-pentyloxy)-;1,2-propanediol, 3-(3-pentyloxy)-; 1,2-propanediol,3-(2-methyl-1-butyloxy)-; 1,2-propanediol, 3-(iso-amyloxy)-;1,2-propanediol, 3-(3-methyl-2-butyloxy)-; 1,2-propanediol,3-(cyclohexyloxy)-; 1,2-propanediol, 3-(1-cyclohex-1-enyloxy)-;1,3-propanediol, 2-(pentyloxy)-; 1,3-propanediol, 2-(2-pentyloxy)-;1,3-propanediol, 2-(3-pentyloxy)-;1,3-propanediol,2-(2-methyl-1-butyloxy)-; 1,3-propanediol,2-(iso-amyloxy)-; 1,3-propanediol, 2-(3-methyl-2-butyloxy)-;1,3-propanediol 2-(cyclohexyloxy)-; 1,3-propanediol,2-(1-cyclohex-1-enyloxy)-; 1,2-propanediol, 3-(butyloxy)-,triethoxylated; 1,2-propanediol, 3-(butyloxy)-, tetraethoxylated;1,2-propanediol, 3-(butyloxy)-, pentaethoxylated; 1,2-propanediol,3-(butyloxy)-, hexaethoxylated; 1,2-propanediol, 3-(butyloxy)-,heptaethoxylated; 1,2-propanediol, 3-(butyloxy)-, octaethoxylated;1,2-propanediol, 3-(butyloxy)-, nonaethoxylated; 1,2-propanediol,3-(butyloxy)-, monopropoxylated; 1,2-propanediol, 3-(butyloxy)-,dibutyleneoxylated; 1,2-propanediol, 3-(butyloxy)-, tributyleneoxylated;1,2-propanediol, 3-phenyloxy-; 1,2-propanediol, 3-benzyloxy-;1,2-propanediol, 3-(2-phenylethyloxy)-; 1,2-propanediol,3-(1-phenyl-2-propanyloxy)-; 1,3-propanediol, 2-phenyloxy-;1,3-propanediol, 2-(m-cresyloxy)-; 1,3-propanediol, 2-(p-cresyloxy)-;1,3-propanediol, -benzyloxy-; 1,3-propanediol, 2-(2-phenylethyloxy)-;1,3-propanediol, 2-(1-phenylethyloxy)-; bis(2-hydroxybutyl)ether; and/orbis(2-hydroxycyclopentyl)ether;

VII. saturated and unsaturated alicyclic diols and their derivativesincluding:

(a) the saturated diols and their derivatives, including:1-isopropyl-1,2-cyclobutanediol; 3-ethyl-4-methyl-1,2-cyclobutanediol;3-propyl-1,2-cyclobutanediol; 3-isopropyl-1,2-cyclobutanediol;1-ethyl-1,2-cyclopentanediol; 1,2-dimethyl-1,2-cyclopentanediol;1,4-dimethyl-1,2-cyclopentanediol; 2,4,5-trimethyl-1,3-cyclopentanediol;3,3-dimethyl-1,2-cyclopentanediol; 3,4-dimethyl-1,2-cyclopentanediol;3,5-dimethyl-1,2-cyclopentanediol; 3-ethyl-1,2-cyclopentanediol;4,4-dimethyl-1,2-cyclopentanediol; 4-ethyl-1,2-cyclopentanediol;1,1-bis(hydroxymethyl)cyclohexane; 1,2-bis(hydroxymethyl)cyclohexane;1,2-dimethyl-1,3-cyclohexanediol; 1,3-bis(hydroxymethyl)cyclohexane;1,3-dimethyl-1,3-cyclohexanediol; 1,6-dimethyl-1,3-cyclohexanediol;1-hydroxy-cyclohexaneethanol; 1-hydroxy-cyclohexanemethanol;1-ethyl-1,3-cyclohexanediol; 1-methyl-1,2-cyclohexanediol;2,2-dimethyl-1,3-cyclohexanediol; 2,3-dimethyl-1,4-cyclohexanediol;2,4-dimethyl-1,3-cyclohexanediol; 2,5-dimethyl-1,3-cyclohexanediol;2,6-dimethyl-1,4-cyclohexanediol; 2-ethyl-1,3-cyclohexanediol;2-hydroxycyclohexaneethanol; 2-hydroxyethyl-1-cyclohexanol;2-hydroxymethylcyclohexanol; 3-hydroxyethyl-1-cyclohexanol;3-hydroxycyclohexaneethanol; 3-hydroxymethylcyclohexanol;3-methyl-1,2-cyclohexanediol; 4,4-dimethyl-1,3-cyclohexanediol;4,5-dimethyl-1,3-cyclohexanediol; 4,6-dimethyl-1,3-cyclohexanediol;4-ethyl-1,3-cyclohexanediol; 4-hydroxyethyl-1-cyclohexanol;4-hydroxymethylcyclohexanol; 4-methyl-1,2-cyclohexanediol;5,5-dimethyl-1,3-cyclohexanediol; 5-ethyl-1,3-cyclohexanediol;1,2-cycloheptanediol; 2-methyl-1,3-cycloheptanediol;2-methyl-1,4-cycloheptanediol; 4-methyl-1,3-cycloheptanediol;5-methyl-1,3-cycloheptanediol; 5-methyl-1,4-cycloheptanediol;6-methyl-1,4-cycloheptanediol; 1,3-cyclooctanediol; 1,4-cyclooctanediol;1,5-cyclooctanediol; 1,2-cyclohexanediol, diethoxylate;1,2-cyclohexanediol, triethoxylate; 1,2-cyclohexanediol,tetraethoxylate; 1,2-cyclohexanediol, pentaethoxylate;1,2-cyclohexanediol, hexaethoxylate; 1,2-cyclohexanediol,heptaethoxylate; 1,2-cyclohexanediol, octaethoxylate;1,2-cyclohexanediol, nonaethoxylate; 1,2-cyclohexanediol,monopropoxylate; 1,2-cyclohexanediol, monobutylenoxylate;1,2-cyclohexanediol, dibutylenoxylate; and/or 1,2-cyclohexanediol,tributylenoxylate; and

(b). the unsaturated alicyclic diols including: 1,2-cyclobutanediol,1-ethenyl-2-ethyl-; 3-cyclobutene-1,2-diol, 1,2,3,4-tetramethyl-;3-cyclobutene-1,2-diol, 3,4-diethyl-; 3-cyclobutene-1,2-diol,3-(1,1-dimethylethyl)-; 3-cyclobutene-1,2-diol, 3-butyl-;1,2-cyclopentanediol, 1,2-dimethyl-4-methylene-; 1,2-cyclopentanediol,1-ethyl-3-methylene-; 1,2-cyclopentanediol, 4-(1-propenyl);3-cyclopentene-1,2-diol, 1-ethyl-3-methyl-; 1,2-cyclohexanediol,1-ethenyl-; 1,2-cyclohexanediol, 1-methyl-3-methylene-;1,2-cyclohexanediol, 1-methyl-4-methylene-; 1,2-cyclohexanediol,3-ethenyl-; 1,2-cyclohexanediol, 4-ethenyl-; 3-cyclohexene-1,2-diol,2,6-dimethyl-; 3-cyclohexene-1,2-diol, 6,6-dimethyl-;4-cyclohexene-1,2-diol, 3,6-dimethyl-; 4-cyclohexene-1,2-diol,4,5-dimethyl-; 3-cyclooctene-1,2-diol; 4-cyclooctene-1,2-diol; and/or5-cyclooctene-1,2-diol;

VIII. Alkoxylated derivatives of C₃₋₈ diols [In the followingdisclosure, “EO” means polyethoxylates, i.e., —(CH₂CH₂O)_(n)H; Me-E_(n)means methyl-capped polyethoxylates —(CH₂CH₂O)_(n)CH₃; “2(Me-En)” means2 Me-En groups needed; “PO” means polypropoxylates, —(CH(CH₃)CH₂O)_(n)H;“BO” means polybutyleneoxy groups, (CH(CH₂CH₃)CH₂O)_(n)H; and “n-BO”means poly(n-butyleneoxy) or poly(tetramethylene)oxy groups—(CH₂CH₂CH₂CH₂O)_(n)H. The use of the term “(C_(X))” herein refers tothe number of carbon atoms in the base material which is alkoxylated.]including:

1,1,2-propanediol (C3) 2(Me-E₁₋₄); 1,2-propanediol (C3) PO₄;1,2-propanediol, 2-methyl-(C4) (Me-E₄₋₁₀); 1,2-propanediol,2-methyl-(C4) 2(Me-E₁); 1,2-propanediol, 2-methyl-(C4) PO₃;1,2-propanediol, 2-methyl-(C4) BO₁; 1,3-propanediol (C3) 2(Me-E₆₋₈);1,3-propanediol (C3) PO₅₋₆; 1,3-propanediol, 2,2-diethyl-(C7) E₁₋₇;1,3-propanediol, 2,2-diethyl-(C7) PO₁; 1,3-propanediol, 2,2-diethyl-(C7)n-BO₁₋₂; 1,3-propanediol, 2,2-dimethyl-(C5) 2(Me E₁₋₂); 1,3-propanediol,2,2-dimethyl-(C5) PO₃₋₄; 1,3-propanediol, 2-(1-methylpropyl)-(C7) E₁₋₇;1,3-propanediol, 2-(1-methylpropyl)-(C7) PO₁; 1,3-propanediol,2-(1-methylpropyl)-(C7) n-BO₁₋₂; 1,3-propanediol,2-(2-methylpropyl)-(C7) E₁₋₇; 1,3-propanediol, 2-(2-methylpropyl)-(C7)PO₁; 1,3-propanediol, 2-(2-methylpropyl)-(C7) n-BO₁₋₂; 1,3-propanediol,2-ethyl-(C5) (Me E₆₋₁₀); 1,3-propanediol, 2-ethyl-(C5) 2(Me E₁);1,3-propanediol, 2-ethyl-(C5) PO₃; 1,3-propanediol,2-ethyl-2-methyl-(C6) (Me E₁₋₆); 1,3-propanediol, 2-ethyl-2-methyl-(C6)PO₂; 1,3-propanediol, 2-ethyl-2-methyl-(C6) BO₁; 1,3-propanediol,2-isopropyl-(C6) (Me E₁₋₆); 1,3-propanediol, 2-isopropyl-(C6) PO₂;1,3-propanediol, 2-isopropyl-(C6) BO₁; 1,3-propanediol, 2-methyl-(C4)2(Me E₂₋₅); 1,3-propanediol, 2-methyl-(C4) PO₄₋₅; 1,3-propanediol,2-methyl-(C4) BO₂; 1,3-propanediol, 2-methyl-2-isopropyl-(C7) E₂₋₉;1,3-propanediol, 2-methyl-2-isopropyl-(C7) PO₁; 1,3-propanediol,2-methyl-2-isopropyl-(C7) n-BO₁₋₃; 1,3-propanediol,2-methyl-2-propyl-(C7) E₁₋₇; 1,3-propanediol, 2-methyl-2-propyl-(C7)PO₁; 1,3-propanediol, 2-methyl-2-propyl-(C7) n-BO₁₋₂; 1,3-propanediol,2-propyl-(C6) (Me E₁₋₄); 1,3-propanediol, 2-propyl-(C6) PO₂;1,3-propanediol, 2-propyl-(C6) BO₁;

2. 1,2-butanediol (C4) (Me E₂₋₈); 1,2-butanediol (C4) PO₂₋₃;1,2-butanediol (C4) BO₁; 1,2-butanediol, 2,3-dimethyl-(C6) E₁₋₆;1,2-butanediol, 2,3-dimethyl-(C6) n-BO₁₋₂; 1,2-butanediol, 2-ethyl-(C6)E₁₋₃; 1,2-butanediol, 2-ethyl-(C6) n-BO₁; 1,2-butanediol, 2-methyl-(C5)(Me E₁₋₂); 1,2-butanediol, 2-methyl-(C5) PO₁; 1,2-butanediol,3,3-dimethyl-(C6) E₁₋₆; 1,2-butanediol, 3,3-dimethyl-(C6) n-BO₁₋₂;1,2-butanediol, 3-methyl-(C5) (Me E₁₋₂); 1,2-butanediol, 3-methyl-(C5)PO₁; 1,3-butanediol (C4) 2(Me E₃₋₆); 1,3-butanediol (C4) PO₅;1,3-butanediol (C4) BO₂; 1,3-butanediol, 2,2,3-trimethyl-(C7) (Me E₁₋₃);1,3-butanediol, 2,2,3-trimethyl-(C7) PO₁₋₂; 1,3-butanediol,2,2-dimethyl-(C6) (Me E₃₋₈); 1,3-butanediol, 2,2-dimethyl-(C6) PO₃;1,3-butanediol, 2,3-dimethyl-(C6) (Me E₃₋₈); 1,3-butanediol,2,3-dimethyl-(C6) PO₃; 1,3-butanediol, 2-ethyl-(C6) (Me E₁₋₆);1,3-butanediol, 2-ethyl-(C6) PO₂₋₃; 1,3-butanediol, 2-ethyl-(C6) BO₁;1,3-butanediol, 2-ethyl-2-methyl-(C7) (Me E₁); 1,3-butanediol,2-ethyl-2-methyl-(C7) PO₁; 1,3-butanediol, 2-ethyl-2-methyl-(C7)n-BO₂₋₄; 1,3-butanediol, 2-ethyl-3-methyl-(C7) (Me E₁); 1,3-butanediol,2-ethyl-3-methyl-(C7) PO₁; 1,3-butanediol, 2-ethyl-3-methyl-(C7)n-BO₂₋₄; 1,3-butanediol, 2-isopropyl-(C7) (Me E₁); 1,3-butanediol,2-isopropyl-(C7) PO₁; 1,3-butanediol, 2-isopropyl-(C7) n-BO₂₋₄;1,3-butanediol, 2-methyl-(C5) 2(Me E₁₋₃); 1,3-butanediol, 2-methyl-(C5)PO₄; 1,3-butanediol, 2-propyl-(C7) E₂₋₉; 1,3-butanediol, 2-propyl-(C7)PO₁; 1,3-butanediol, 2-propyl-(C7) n-BO₁₋₃; 1,3-butanediol,3-methyl-(C5) 2(Me E₁₋₃); 1,3-butanediol, 3-methyl-(C5) PO₄;1,4-butanediol (C4) 2(Me E₂₋₄); 1,4-butanediol (C4) PO₄₋₅;1,4-butanediol (C4) BO₂; 1,4-butanediol, 2,2,3-trimethyl-(C7) E₂₋₉;1,4-butanediol, 2,2,3-trimethyl-(C7) PO₁; 1,4-butanediol,2,2,3-trimethyl-(C7) n-BO₁₋₃; 1,4-butanediol, 2,2-dimethyl-(C6) (MeE₁₋₆); 1,4-butanediol, 2,2-dimethyl-(C6) PO₂; 1,4-butanediol,2,2-dimethyl-(C6) BO₁; 1,4-butanediol, 2,3-dimethyl-(C6) (Me E₁₋₆);1,4-butanediol, 2,3-dimethyl-(C6) PO₂; 1,4-butanediol, 2,3-dimethyl-(C6)BO₁; 1,4-butanediol, 2-ethyl-(C6) (Me E₁₋₄); 1,4-butanediol,2-ethyl-(C6) PO₂; 1,4-butanediol, 2-ethyl-(C6) BO₁; 1,4-butanediol,2-ethyl-2-methyl-(C7) E₁₋₇; 1 ,4-butanediol, 2-ethyl-2-methyl-(C7) PO₁;1,4-butanediol, 2-ethyl-2-methyl-(C7) n-BO₁₋₂; 1,4-butanediol,2-ethyl-3-methyl-(C7) E₁₋₇; 1,4-butanediol, 2-ethyl-3-methyl-(C7) PO₁;1,4-butanediol, 2-ethyl-3-methyl-(C7) n-BO₁-₂; 1,4-butanediol,2-isopropyl-(C7) E₁₋₇; 1,4-butanediol, 2-isopropyl-(C7) PO₁;1,4-butanediol, 2-isopropyl-(C7) n-BO₁₋₂; 1,4-butanediol, 2-methyl-(C5)(Me E₆₋₁₀); 1,4-butanediol, 2-methyl-(C5) 2(Me E₁); 1,4-butanediol,2-methyl-(C5) PO₃; 1,4-butanediol, 2-methyl-(C5) BO₁; 1,4-butanediol,2-propyl-(C7) E₁₋₅; 1,4-butanediol, 2-propyl-(C7) n-BO₁₋₂;1,4-butanediol, 3-ethyl-1-methyl-(C7) E₂₋₉; 1,4-butanediol,3-ethyl-1-methyl-(C7) PO₁; 1,4-butanediol, 3-ethyl-1-methyl-(C7)n-BO₁₋₃; 2,3-butanediol (C4) (Me E₆₋₁₀); 2,3-butanediol (C4) 2(Me E₁);2,3-butanediol (C4) PO₃₋₄; 2,3-butanediol (C4) BO₁; 2,3-butanediol,2,3-dimethyl-(C6) E₃₋₉; 2,3-butanediol, 2,3-dimethyl-(C6) PO₁;2,3-butanediol, 2,3-dimethyl-(C6) n-BO₁₋₃; 2,3-butanediol, 2-methyl-(C5)(Me E₅); 2,3-butanediol, 2-methyl-(C5) PO₂; 2,3-butanediol,2-methyl-(C5) BO₁;

3. 1,2-pentanediol (C5) E₃₋₁₀; 1,2-pentanediol, (C5) PO₁;1,2-pentanediol, (C5) n-BO₂₋₃; 1,2-pentanediol, 2-methyl (C6) E₁₋₃;1,2-pentanediol, 2-methyl (C6) n-BO₁; 1,2-pentanediol, 2-methyl (C6)BO₁; 1,2-pentanediol, 3-methyl (C6) E₁₋₃; 1,2-pentanediol, 3-methyl (C6)n-BO₁; 1,2-pentanediol, 4-methyl (C6) E₁₋₃; 1,2-pentanediol, 4-methyl(C6) n-BO₁; 1,3-pentanediol (C5) 2(Me-E₁₋₂); 1,3-pentanediol (C5) PO₃₋₄;1,3-pentanediol, 2,2-dimethyl-(C7) (Me-E₁); 1,3-pentanediol,2,2-dimethyl-(C7) PO₁; 1,3-pentanediol, 2,2-dimethyl-(C7) n-BO₂₋₄;1,3-pentanediol, 2,3-dimethyl-(C7) (Me-E₁); 1,3-pentanediol,2,3-dimethyl-(C7) PO₁; 1,3-pentanediol, 2,3-dimethyl-(C7) n-BO₂₋₄;1,3-pentanediol, 2,4-dimethyl-(C7) (Me-E₁); 1,3-pentanediol,2,4-dimethyl-(C7) PO₁; 1,3-pentanediol, 2,4-dimethyl-(C7) n-BO₂₋₄;1,3-pentanediol, 2-ethyl-(C7) E₂₋₉; 1,3-pentanediol, 2-ethyl-(C7) PO₁;1,3-pentanediol, 2-ethyl-(C7) n-BO₁₋₃; 1,3-pentanediol, 2-methyl-(C6)2(Me-E₁₋₆); 1,3-pentanediol, 2-methyl-(C6) PO₂₋₃; 1,3-pentanediol,2-methyl-(C6) BO₁; 1,3-pentanediol, 3,4-dimethyl-(C7) (Me-E₁);1,3-pentanediol, 3,4-dimethyl-(C7) PO₁; 1,3-pentanediol,3,4-dimethyl-(C7) n-BO₂₋₄; 1,3-pentanediol, 3-methyl-(C6) (Me-E₁₋₆);1,3-pentanediol, 3-methyl-(C6) PO₂₋₃; 1,3-pentanediol, 3-methyl-(C6)BO₁; 1,3-pentanediol, 4,4-dimethyl-(C7) (Me-E₁); 1,3-pentanediol,4,4-dimethyl-(C7) PO₁; 1,3-pentanediol, 4,4-dimethyl-(C7) n-BO₂₋₄;1,3-pentanediol, 4-methyl-(C6) (Me-E₁₋₆); 1,3-pentanediol, 4-methyl-(C6)PO₂₋₃; 1,3-pentanediol, 4-methyl-(C6) BO₁; 1,4-pentanediol, (C5)2(Me-E₁₋₂); 1,4-pentanediol (C5) PO₃₋₄; 1,4-pentanediol,2,2-dimethyl-(C7) (Me-E₁); 1,4-pentanediol, 2,2-dimethyl-(C7) PO₁;1,4-pentanediol, 2,2-dimethyl-(C7) n-BO₂₋₄; 1,4-pentanediol,2,3-dimethyl (C7) (Me-E₁); 1,4-pentanediol, 2,3-dimethyl (C7) PO₁;1,4-pentanediol, 2,3-dimethyl-(C7) n-BO₂₋₄; 1,4-pentanediol,2,4-dimethyl-(C7) (Me-E₁); 1,4-pentanediol, 2,4-dimethyl-(C7) PO₁;1,4-pentanediol, 2,4-dimethyl-(C7) n-BO₂₋₄; 1,4-pentanediol,2-methyl-(C6) (Me-E₁₋₆); 1,4-pentanediol, 2-methyl-(C6) PO₂₋₃;1,4-pentanediol, 2-methyl-(C6) BO₁; 1,4-pentanediol, 3,3-dimethyl-(C7)(Me-E₁); 1,4-pentanediol, 3,3-dimethyl-(C7) PO₁; 1,4-pentanediol,3,3-dimethyl-(C7) n-BO₂₋₄; 1,4-pentanediol, 3,4-dimethyl (C7) (Me-E₁);1,4-pentanediol, 3,4-dimethyl-(C7) PO₁; 1,4-pentanediol,3,4-dimethyl-(C7) n-BO₂ ₄; 1,4-pentanediol, 3-methyl-(C6) 2(Me-E₁₋₆);1,4-pentanediol, 3-methyl-(C6) PO₂₋₃; 1,4-pentanediol, 3-methyl-(C6)BO₁; 1,4-pentanediol, 4-methyl-(C6) 2(Me-E₁₋₆); 1,4-pentanediol,4-methyl-(C6) PO₂₋₃; 1,4-pentanediol, 4-methyl-(C6) BO₁;1,5-pentanediol, (C5) (Me-E₄₋₁₀); 1,5-pentanediol (C5) 2(Me—E₁);1,5-pentanediol (C5) PO₃; 1,5-pentanediol, 2,2-dimethyl-(C7) E₁₋₇;1,5-pentanediol, 2,2-dimethyl-(C7) PO₁; 1,5-pentanediol,2,2-dimethyl-(C7) n-BO₁₋₂; 1,5-pentanediol, 2,3-dimethyl-(C7) E₁₋₇;1,5-pentanediol, 2,3-dimethyl-(C7) PO₁; 1,5-pentanediol,2,3-dimethyl-(C7) n-BO₁₋₂; 1,5-pentanediol, 2,4-dimethyl-(C7) E₁₋₇;1,5-pentanediol, 2,4-dimethyl-(C7) PO₁; 1,5-pentanediol,2,4-dimethyl-(C7) n-BO₁₋₂; 1,5-pentanediol, 2-ethyl-(C7) E₁₋₅;1,5-pentanediol, 2-ethyl-(C7) n-BO₁₋₂; 1,5-pentanediol, 2-methyl-(C6)(Me-E₁₋₄); 1,5-pentanediol, 2-methyl-(C6) PO₂; 1,5-pentanediol,3,3-dimethyl-(C7) E₁₋₇; 1,5-pentanediol, 3,3-dimethyl-(C7) PO₁;1,5-pentanediol, 3,3-dimethyl-(C7) n-BO₁₋₂; 1,5-pentanediol,3-methyl-(C6) (Me-E₁₋₄); 1,5-pentanediol, 3-methyl-(C6) PO₂;2,3-pentanediol, (C5) (Me-E₁₋₃); 2,3-pentanediol, (C5) PO₂;2,3-pentanediol, 2-methyl-(C6) E₁₋₇; 2,3-pentanediol, 2-methyl-(C6) PO₁;2,3-pentanediol, 2-methyl-(C6) n-BO₁₋₂; 2,3-pentanediol, 3-methyl-(C6)E₁₋₇; 2,3-pentanediol, 3-methyl-(C6) PO₁; 2,3-pentanediol, 3-methyl-(C6)n-BO₁₋₂; 2,3-pentanediol, 4-methyl-(C6) E₁₋₇; 2,3-pentanediol,4-methyl-(C6) PO₁; 2,3-pentanediol, 4-methyl-(C6) n-BO₁₋₂;2,4-pentanediol, (C5) 2(Me-E₁₋₄); 2,4-pentanediol (C5) PO₄;2,4-pentanediol, 2,3-dimethyl-(C7) (Me-E₁₋₄); 2,4-pentanediol,2,3-dimethyl-(C7) PO₂; 2,4-pentanediol, 2,4-dimethyl-(C7) (Me—E₁₋₄);2,4-pentanediol, 2,4-dimethyl-(C7) PO₂; 2,4-pentanediol, 2(Me-E₅₋₁₀);2,4-pentanediol, 2-methyl-(C7) PO₃; 2,4-pentanediol, 3,3-dimethyl-(C7)(Me-E₁₋₄); 2,4-pentanediol, 3,3-dimethyl-(C7) PO₂; 2,4-pentanediol,3-methyl-(C6) (Me-E₅₋₁₀); 2,4-pentanediol, 3-methyl-(C6) PO₃;

4. 1,3-hexanediol (C6) (Me-E₁₋₅); 1,3-hexanediol (C6) PO₂;1,3-hexanediol (C6) BO₁; 1,3-hexanediol, 2-methyl-(C7) E₂₋₉;1,3-hexanediol, 2-methyl-(C7) PO₁; 1,3-hexanediol, 2-methyl-(C7)n-BO₁₋₃; 1,3-hexanediol, 2-methyl-(C7) BO₁; 1,3-hexanediol,3-methyl-(C7) E₂₋₉; 1,3-hexanediol, 3-methyl-(C7) PO₁; 1,3-hexanediol,3-methyl-(C7) n-BO₁₋₃; 1,3-hexanediol, 4-methyl-(C7) E₂₋₉;1,3-hexanediol, 4-methyl-(C7) PO₁; 1,3-hexanediol, 4-methyl-(C7)n-BO₁₋₃; 1,3-hexanediol, 5-methyl-(C7) E₂₋₉; 1,3-hexanediol,5-methyl-(C7) PO₁; 1,3-hexanediol, 5-methyl-(C7) n-BO₁₋₃; 1,4-hexanediol(C6) (Me-E₁₋₅); 1,4-hexanediol (C6) PO₂; 1,4-hexanediol (C6) BO₁;1,4-hexanediol, 2-methyl-(C7) E₂₋₉; 1,4-hexanediol, 2-methyl-(C7) PO₁;1,4-hexanediol, 2-methyl-(C7) n-BO₁₋₃; 1,4-hexanediol, 3-methyl-(C7)E₂₋₉; 1,4-hexanediol, 3-methyl-(C7) PO₁; 1,4-hexanediol, 3-methyl-(C7)n-BO₁₋₃; 1,4-hexanediol, 4-methyl-(C7) E₂₋₉; 1,4-hexanediol,4-methyl-(C7) PO₁; 1,4-hexanediol, 4-methyl-(C7) n-BO₁₋₃;1,4-hexanediol, 5-methyl-(C7) E₂₋₉; 1,4-hexanediol, 5-methyl-(C7) PO₁;1,4-hexanediol, 5-methyl-(C7) n-BO₁₋₃; 1,5-hexanediol (C6) (Me-E₁₋₅);1,5-hexanediol (C6) PO₂; 1,5-hexanediol (C6) BO₁; 1,5-hexanediol,2-methyl-(C7) E₂₋₉; 1,5-hexanediol, 2-methyl-(C7) PO₁; 1,5-hexanediol,2-methyl-(C7) n-BO₁₋₃; 1,5-hexanediol, 3-methyl-(C7) E₂₋₉;1,5-hexanediol, 3-methyl-(C7) PO₁; 1,5-hexanediol, 3-methyl-(C7)n-BO₁₋₃; 1,5-hexanediol, 4-methyl-(C7) E₂₋₉; 1,5-hexanediol,4-methyl-(C7) PO₁; 1,5-hexanediol, 4-methyl-(C7) n-BO₁₋₃;1,5-hexanediol, 5-methyl-(C7) E₂₋₉; 1,5-hexanediol, 5-methyl-(C7) PO₁;1,5-hexanediol, 5-methyl-(C7) n-BO₁₋₃; 1,6-hexanediol (C6) (Me-E₁₋₂);1,6-hexanediol (C6) PO₁₋₂; 1,6-hexanediol (C6) n-BO₄; 1,6-hexanediol,2-methyl-(C7) E₁₋₅; 1,6-hexanediol, 2-methyl-(C7) n-BO₁₋₂;1,6-hexanediol, 3-methyl-(C7) E₁₋₅; 1,6-hexanediol, 3-methyl-(C7)n-BO₁₋₂; 2,3-hexanediol (C6) E₁₋₅; 2,3-hexanediol (C6) n-BO₁;2,3-hexanediol (C6) BO₁; 2,4-hexanediol (C6) (Me-E₃₋₈); 2,4-hexanediol(C6) PO₃; 2,4-hexanediol, 2-methyl-(C7) (Me-E₁₋₂); 2,4-hexanediol2-methyl-(C7) PO₁₋₂; 2,4-hexanediol, 3-methyl-(C7) (Me-E₁₋₂);2,4-hexanediol 3-methyl-(C7) PO₁₋₂; 2,4-hexanediol, 4-methyl-(C7)(Me-E₁₋₂); 2,4-hexanediol 4-methyl-(C7) PO₁₋₂; 2,4-hexanediol,5-methyl-(C7) (Me-E₁₋₂); 2,4-hexanediol 5-methyl-(C7) PO₁₋₂;2,5-hexanediol (C6) (Me-E₃₋₈); 2,5-hexanediol (C6) PO₃; 2,5-hexanediol,2-methyl-(C7) (Me-E₁₋₂); 2,5-hexanediol 2-methyl-(C7) PO₁₋₂;2,5-hexanediol, 3-methyl-(C7) (Me-E₁₋₂); 2,5-hexanediol 3-methyl-(C7)PO₁₋₂; 3,4-hexanediol (C6) EO₁₋₅; 3,4-hexanediol (C6) n-BO₁;3,4-hexanediol (C6) BO₁;

5. 1,3-heptanediol (C7) E₁₋₇; 1,3-heptanediol (C7) PO₁; 1,3-heptanediol(C7) n-BO₁₋₂; 1,4-heptanediol (C7) E₁₋₇; 1,4-heptanediol (C7) PO₁;1,4-heptanediol (C7) n-BO₁₋₂; 1,5-heptanediol (C7) E₁₋₇; 1,5-heptanediol(C7) PO₁; 1,5-heptanediol (C7) n-BO₁₋₂; 1,6-heptanediol (C7) E₁₋₇;1,6-heptanediol (C7) PO₁; 1,6-heptanediol (C7) n-BO₁₋₂; 1,7-heptanediol(C7) E₁₋₂; 1,7-heptanediol (C7) n-BO₁; 2,4-heptanediol (C7) E₃₋₁₀;2,4-heptanediol (C7) (Me-E₁); 2,4-heptanediol (C7) PO₁; 2,4-heptanediol(C7) n-BO₃; 2,5-heptanediol (C7) E₃₋₁₀; 2,5-heptanediol (C7) (Me-E₁);2,5-heptanediol (C7) PO₁; 2,5-heptanediol (C7) n-BO₃; 2,6-heptanediol(C7) E₃₋₁₀; 2,6-heptanediol (C7) (Me-E₁); 2,6-heptanediol (C7) PO₁;2,6-heptanediol (C7) n-BO₃; 3,5-heptanediol (C7) E₃₋₁₀; 3,5-heptanediol(C7) (Me-E₁); 3,5-heptanediol (C7) PO₁; 3,5-heptanediol (C7) n-BO₃;

6. 1,3-butanediol, 3-methyl-2-isopropyl-(C8) PO₁; 2,4-pentanediol,2,3,3-trimethyl-(C8) PO₁; 1,3-butanediol, 2,2-diethyl-(C8) E₂₋₅;2,4-hexanediol, 2,3-dimethyl-(C8) E₂₋₅; 2,4-hexanediol,2,4-dimethyl-(C8) E₂₋₅; 2,4-hexanediol, 2,5-dimethyl-(C8) E₂₋₅;2,4-hexanediol, 3,3-dimethyl-(C8) E₂₋₅; 2,4-hexanediol,3,4-dimethyl-(C8) E₂₋₅; 2,4-hexanediol, 3,5-dimethyl-(C8) E₂₋₅;2,4-hexanediol, 4,5-dimethyl-(C8) E₂₋₅; 2,4-hexanediol,5,5-dimethyl-(C8) E₂₋₅; 2,5-hexanediol, 2,3-dimethyl-(C8) E₂₋₅;2,5-hexanediol, 2,4-dimethyl-(C8) E₂₋₅; 2,5-hexanediol,2,5-dimethyl-(C8) E₂₋₅; 2,5-hexanediol, 3,3-dimethyl-(C8) E₂₋₅;2,5-hexanediol, 3,4-dimethyl-(C8) E₂₋₅; 3,5-heptanediol, 3-methyl-(C8)E₂₋₅; 1,3-butanediol, 2,2-diethyl-(C8) n-BO₁₋₂; 2,4-hexanediol,2,3-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol, 2,4-dimethyl-(C8) n-BO₁₋₂;2,4-hexanediol, 2,5-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol,3,3-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol, 3,4-dimethyl-(C8) n-BO₁₋₂;2,4-hexanediol, 3,5-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol,4,5-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol, 5,5-dimethyl-, n-BO₁₋₂;2,5-hexanediol, 2,3-dimethyl-(C8) n-BO₁-₂; 2,5-hexanediol,2,4-dimethyl-(C8) n-BO₁₋₂; 2,5-hexanediol, 2,5-dimethyl-(C8) n-BO₁₋₂;2,5-hexanediol, 3,3-dimethyl-(C8) n-BO₁₋₂; 2,5-hexanediol,3,4-dimethyl-(C8) n-BO₁₋₂; 3,5-heptanediol, 3-methyl-(C8) n-BO₁₋₂;1,3-propanediol, 2-(1,2-dimethylpropyl)-(C8) n-BO₁; 1,3-butanediol,2-ethyl-2,3-dimethyl-(C8) n-BO₁; 1,3-butanediol,2-methyl-2-isopropyl-(C8) n-BO₁; 1,4-butanediol,3-methyl-2-isopropyl-(C8) n-BO₁; 1,3-pentanediol, 2,2,3-trimethyl-(C8)n-BO₁; 1,3-pentanediol, 2,2,4-trimethyl-(C8) n-BO₁; 1,3-pentanediol,2,4,4-trimethyl-(C8) n-BO₁; 1,3-pentanediol, 3,4,4-trimethyl-(C8) n-BO₁;1,4-pentanediol, 2,2,3-trimethyl-(C8) n-BO₁; 1,4-pentanediol,2,2,4-trimethyl-(C8) n-BO₁; 1,4-pentanediol, 2,3,3-trimethyl-(C8) n-BO₁;1,4-pentanediol, 2,3,4-trimethyl-(C8) n-BO₁; 1,4-pentanediol,3,3,4-trimethyl-(C8) n-BO₁; 2,4-pentanediol, 2,3,4-trimethyl-(C8) n-BO₁;2,4-hexanediol, 4-ethyl-(C8) n-BO₁; 2,4-heptanediol, 2-methyl-(C8)n-BO₁; 2,4-heptanediol, 3-methyl-(C8) n-BO₁; 2,4-heptanediol,4-methyl-(C8) n-BO₁; 2,4-heptanediol, 5-methyl-(C8) n-BO₁;2,4-heptanediol, 6-methyl-(C8) n-BO₁; 2,5-heptanediol, 2-methyl-(C8)n-BO₁; 2,5-heptanediol, 3-methyl-(C8) n-BO₁; 2,5-heptanediol,4-methyl-(C8) n-BO₁; 2,5-heptanediol, 5-methyl-(C8) n-BO₁;2,5-heptanediol, 6-methyl-(C8) n-BO₁; 2,6-heptanediol, 2-methyl-(C8)n-BO₁; 2,6-heptanediol, 3-methyl-(C8) n-BO₁; 2,6-heptanediol,4-methyl-(C8) n-BO₁; 3,5-heptanediol, 2-methyl-(C8) n-BO₁;1,3-propanediol, 2-(1,2-dimethylpropyl)-(C8) E₁₋₃; 1,3-butanediol,2-ethyl-2,3-dimethyl-(C8) E₁₋₃; 1,3-butanediol,2-methyl-2-isopropyl-(C8) E₁₋₃; 1,4-butanediol,3-methyl-2-isopropyl-(C8) E₁₋₃; 1,3-pentanediol, 2,2,3-trimethyl-(C8)E₁₋₃; 1,3-pentanediol, 2,2,4-trimethyl-(C8) E₁₋₃; 1,3-pentanediol,2,4,4-trimethyl-(C8) E₁₋₃; 1,3-pentanediol, 3,4,4-trimethyl-(C8) E₁₋₃;1,4-pentanediol, 2,2,3-trimethyl-(C8) E₁₋₃; 1,4-pentanediol,2,2,4-trimethyl-(C8) E₁₋₃; 1,4-pentanediol, 2,3,3-trimethyl-(C8) E₁₋₃;1,4-pentanediol, 2,3,4-trimethyl-(C8) E₁₋₃; 1,4-pentanediol,3,3,4-trimethyl-(C8) E₁₋₃; 2,4-pentanediol, 2,3,4-trimethyl-(C8) E₁₋₃;2,4-hexanediol, 4-ethyl-(C8) E₁₋₃; 2,4-heptanediol, 2-methyl-(C8) E₁₋₃;2,4-heptanediol, 3-methyl-(C8) E₁₋₃; 2,4-heptanediol, 4-methyl-(C8)E₁₋₃; 2,4-heptanediol, 5-methyl-(C8) E₁₋₃; 2,4-heptanediol,6-methyl-(C8) E₁₋₃; 2,5-heptanediol, 2-methyl-(C8) E₁₋₃;2,5-heptanediol, 3-methyl-(C8) E₁₋₃; 2,5-heptanediol, 4-methyl-(C8)E₁₋₃; 2,5-heptanediol, 5-methyl-(C8) E₁₋₃; 2,5-heptanediol,6-methyl-(C8) E₁₋₃; 2,6-heptanediol, 2-methyl-(C8) E₁₋₃;2,6-heptanediol, 3-methyl-(C8) E₁₋₃; 2,6-heptanediol, 4-methyl-(C8)E₁₋₃; and/or 3,5-heptanediol, 2-methyl-(C8) E₁₋₃; and

7. mixtures thereof;

IX. aromatic diols including: 1-phenyl-1,2-ethanediol;1-phenyl-1,2-propanediol; 2-phenyl-1,2-propanediol;3-phenyl-1,2-propanediol; 1-(3-methylphenyl)-1,3-propanediol;1-(4-methylphenyl)-1,3-propanediol; 2-methyl-1-phenyl-1,3-propanediol;1-phenyl-1,3-butanediol; 3-phenyl-1,3-butanediol;1-phenyl-1,4-butanediol; 2-phenyl-1,4-butanediol; and/or1-phenyl-2,3-butanediol;

X. principal solvents which are homologs, or analogs, of the abovestructures where one, or more, CH₂ groups are added while, for each CH₂group added, two hydrogen atoms are removed from adjacent carbon atomsin the molecule to form one carbon-carbon double bond, thus holding thenumber of hydrogen atoms in the molecule constant, including thefollowing:

1,3-Propanediol, 2,2-di-2-propenyl-; 1,3-Propanediol, 2-(1-pentenyl)-;1,3-Propanediol, 2-(2-methyl-2-propenyl)-2-(2-propenyl)-;1,3-Propanediol, 2-(3-methyl-1-butenyl)-; 1,3-Propanediol,2-(4-pentenyl)-; 1,3-Propanediol, 2-ethyl-2-(2-methyl-2-propenyl)-;1,3-Propanediol, 2-ethyl-2-(2-propenyl)-; 1,3-Propanediol,2-methyl-2-(3-methyl-3-butenyl)-; 1,3-Butanediol, 2,2-diallyl-;1,3-Butanediol, 2-(1-ethyl-1-propenyl)-; 1,3-Butanediol,2-(2-butenyl)-2-methyl-; 1,3-Butanediol, 2-(3-methyl-2-butenyl)-;1,3-Butanediol, 2-ethyl-2-(2-propenyl)-; 1,3-Butanediol,2-methyl-2-(1-methyl-2-propenyl)-; 1,4-Butanediol,2,3-bis(1-methylethylidene)-; 1,4-Butanediol,2-(3-methyl-2-butenyl)-3-methylene-; 2-Butene-1,4-diol,2-(1,1-dimethylpropyl)-; 2-Butene-1,4-diol, 2-(1-methylpropyl)-;2-Butene-1,4-diol, 2-butyl-; 1,3-Pentanediol, 2-ethenyl-3-ethyl-;1,3-Pentanediol, 2-ethenyl-4,4-dimethyl-; 1,4-Pentanediol,3-methyl-2-(2-propenyl)-; 1,5-Pentanediol, 2-(1-propenyl)-;1,5-Pentanediol, 2-(2-propenyl)-; 1,5-Pentanediol,2-ethylidene-3-methyl-; 1,5-Pentanediol, 2-propylidene-;2,4-Pentanediol, 3-ethylidene-2,4-dimethyl-; 4-Pentene-1,3-diol,2-(1,1-dimethylethyl)-; 4-Pentene-1,3-diol, 2-ethyl-2,3-dimethyl-;1,4-Hexanediol, 4-ethyl-2-methylene-; 1,5-Hexadiene-3,4-diol,2,3,5-trimethyl-; 1,5-Hexadiene-3,4-diol, 5-ethyl-3-methyl-;1,5-Hexanediol, 2-(1-methylethenyl)-; 1,6-Hexanediol, 2-ethenyl-;1-Hexene-3,4-diol, 5,5-dimethyl-; 1-Hexene-3,4-diol, 5,5-dimethyl-;2-Hexene-1,5-diol, 4-ethenyl-2,5-dimethyl-; 3-Hexene-1,6-diol,2-ethenyl-2,5-dimethyl-; 3-Hexene-1,6-diol, 2-ethyl-; 3-Hexene-1,6-diol,3,4-dimethyl-; 4-Hexene-2,3-diol, 2,5-dimethyl-; 4-Hexene-2,3-diol,3,4-dimethyl-; 5-Hexene-1,3-diol, 3-(2-propenyl)-; 5-Hexene-2,3-diol,2,3-dimethyl-; 5-Hexene-2,3-diol, 3,4-dimethyl-; 5-Hexene-2,3-diol,3,5-dimethyl-; 5-Hexene-2,4-diol, 3-ethenyl-2,5-dimethyl-;1,4-Heptanediol, 6-methyl-5-methylene-; 1,5-Heptadiene-3,4-diol,2,3-dimethyl-; 1,5-Heptadiene-3,4-diol, 2,5-dimethyl-;1,5-Heptadiene-3,4-diol, 3,5-dimethyl-; 1,7-Heptanediol,2,6-bis(methylene)-; 1,7-Heptanediol, 4-methylene-; 1-Heptene-3,5-diol,2,4-dimethyl-; 1-Heptene-3,5-diol, 2,6-dimethyl-; 1-Heptene-3,5-diol,3-ethenyl-5-methyl; 1-Heptene-3,5-diol, 6,6-dimethyl-;2,4-Heptadiene-2,6-diol, 4,6-dimethyl-; 2,5-Heptadiene-1,7-diol,4,4-dimethyl-; 2,6-Heptadiene-1,4-diol, 2,5,5-trimethyl-;2-Heptene-1,4-diol, 5,6-dimethyl-; 2-Heptene-1,5-diol, 5-ethyl-;2-Heptene-1,7-diol, 2-methyl-; 3-Heptene-1,5-diol, 4,6-dimethyl-;3-Heptene-1,7-diol, 3-methyl-6-methylene-; 3-Heptene-2,5-diol,2,4-dimethyl-; 3-Heptene-2,5-diol, 2,5-dimethyl-; 3-Heptene-2,6-diol,2,6-dimethyl-; 3-Heptene-2,6-diol, 4,6-dimethyl-; 5-Heptene-1,3-diol,2,4-dimethyl-; 5-Heptene-1,3-diol, 3,6-dimethyl-; 5-Heptene-1,4-diol,2,6-dimethyl-; 5-Heptene-1,4-diol, 3,6-dimethyl-; 5-Heptene-2,4-diol,2,3-dimethyl-; 6-Heptene-1,3-diol, 2,2-dimethyl-; 6-Heptene-1,4-diol,4-(2-propenyl)-; 6-Heptene-1,4-diol, 5,6-dimethyl-; 6-Heptene-1,5-diol,2,4-dimethyl-; 6-Heptene-1,5-diol, 2-ethylidene-6-methyl-;6-Heptene-2,4-diol, 4-(2-propenyl)-; 6-Heptene-2,4-diol, 5,5-dimethyl-;6-Heptene-2,5-diol, 4,6-dimethyl-; 6-Heptene-2,5-diol,5-ethenyl-4-methyl-; 1,3-Octanediol, 2-methylene-;1,6-Octadiene-3,5-diol, 2,6-dimethyl-; 1,6-Octadiene-3,5-diol,3,7-dimethyl-; 1,7-Octadiene-3,6-diol, 2,6-dimethyl-;1,7-Octadiene-3,6-diol, 2,7-dimethyl-; 1,7-Octadiene-3,6-diol,3,6-dimethyl-; 1-Octene-3,6-diol, 3-ethenyl-; 2,4,6-Octatriene-1,8-diol,2,7-dimethyl-; 2,4-Octadiene-1,7-diol, 3,7-dimethyl-;2,5-Octadiene-1,7-diol, 2,6-dimethyl-; 2,5-Octadiene-1,7-diol,3,7-dimethyl-; 2,6-Octadiene-1,4-diol, 3,7-dimethyl-(Rosiridol);2,6-Octadiene-1,8-diol, 2-methyl-; 2,7-Octadiene-1,4-diol,3,7-dimethyl-; 2,7-Octadiene-1,5-diol, 2,6-dimethyl-;2,7-Octadiene-1,6-diol, 2,6-dimethyl-(8-Hydroxylinalool);2,7-Octadiene-1,6-diol, 2,7-dimethyl-; 2-Octene-1,4-diol;2-Octene-1,7-diol; 2-Octene-1,7-diol, 2-methyl-6-methylene-;3,5-Octadiene-1,7-diol, 3,7-dimethyl-; 3,5-Octadiene-2,7-diol,2,7-dimethyl-; 3,5-Octanediol, 4-methylene-; 3,7-Octadiene-1,6-diol,2,6-dimethyl-; 3,7-Octadiene-2,5-diol, 2,7-dimethyl-;3,7-Octadiene-2,6-diol, 2,6-dimethyl-; 3-Octene-1,5-diol, 4-methyl-;3-Octene-1,5-diol, 5-methyl-; 4,6-Octadiene-1,3-diol, 2,2-dimethyl-;4,7-Octadiene-2,3-diol, 2,6-dimethyl-; 4,7-Octadiene-2,6-diol,2,6-dimethyl-; 4-Octene-1,6-diol, 7-methyl-; 2,7-bis(methylene)-;2-methylene-; 5,7-Octadiene-1,4-diol, 2,7-dimethyl-;5,7-Octadiene-1,4-diol, 7-methyl-; 5-Octene-1,3-diol; 6-Octene-1,3-diol,7-methyl-; 6-Octene-1,4-diol, 7-methyl-; 6-Octene-1,5-diol;6-Octene-1,5-diol, 7-methyl-; 6-Octene-3,5-diol, 2-methyl-;6-Octene-3,5-diol, 4-methyl-; 7-Octene-1,3-diol, 2-methyl-;7-Octene-1,3-diol, 4-methyl-; 7-Octene-1,3-diol, 7-methyl-;7-Octene-1,5-diol; 7-Octene-1,6-diol; 7-Octene-1,6-diol, 5-methyl-;7-Octene-2,4-diol, 2-methyl-6-methylene-; 7-Octene-2,5-diol, 7-methyl-;7-Octene-3,5-diol, 2-methyl-; 1-Nonene-3,5-diol; 1-Nonene-3,7-diol;3-Nonene-2,5-diol; 4,6-Nonadiene-1,3-diol, 8-methyl-; 4-Nonene-2,8-diol;6,8-Nonadiene-1,5-diol; 7-Nonene-2,4-diol; 8-Nonene-2,4-diol;8-Nonene-2,5-diol; 1,9-Decadiene-3,8-diol; and/or1,9-Decadiene-4,6-diol; and

XI. mixtures thereof;

C. optionally, but preferably, an effective amount, sufficient toimprove clarity, of low molecular weight water soluble solvents likeethanol, isopropanol, propylene glycol, 1,3-propanediol, propylenecarbonate, etc., said water soluble solvents being at a level that willnot form clear compositions by themselves;

D. optionally, but preferably, from 0% to about 15%, preferably fromabout 0.1% to about 8%, and more preferably from about 0.2% to about 5%,of perfume;

E. optionally, from 0% to about 2%, preferably from about 0.01% to about0.2%, and more preferably from about 0.035% to about 0.1%, ofstabilizer;

F. optionally, but preferably, an effective amount to improve clarity,of water soluble calcium and/or magnesium salt, preferably chloride; and

G. the balance being water.

Preferably, the compositions herein are aqueous, translucent or clear,preferably clear, compositions containing from about 3% to about 95%,preferably from about 5% to about 80%, more preferably from about 15% toabout 70%, and even more preferably from about 40% to about 60%, waterand from about 3% to about 40%, preferably from about 10% to about 35%,more preferably from about 12% to about 25%, and even more preferablyfrom about 14% to about 20%, of the above principal alcohol solvent B.These preferred products (compositions) are not translucent or clearwithout principal solvent B. The amount of principal solvent B. requiredto make the compositions translucent or clear is preferably more than50%, more preferably more than about 60%, and even more preferably morethan about 75%, of the total organic solvent present.

The principal solvents are desirably kept to the lowest levels thatprovide acceptable stability/clarity in the present compositions. Thepresence of water exerts an important effect on the need for theprincipal solvents to achieve clarity of these compositions. The higherthe water content, the higher the principal solvent level (relative tothe softener level) is needed to attain product clarity. Inversely, theless the water content, the less principal solvent (relative to thesoftener) is needed. Thus, at low water levels of from about 5% to about15%, the softener active-to-principal solvent weight ratio is preferablyfrom about 55:45 to about 85:15, more preferably from about 60:40 toabout 80:20. At water levels of from about 15% to about 70%, thesoftener active-to-principal solvent weight ratio is preferably fromabout 45:55 to about 70:30, more preferably from about 55:45 to about70:30. But at high water levels of from about 70% to about 80%, thesoftener active-to-principal solvent weight ratio is preferably fromabout 30:70 to about 55:45, more preferably from about 35:65 to about45:55. At higher water levels, the softener to principal solvent ratiosshould be even higher.

The pH of the compositions should be from about 1 to about 7, preferablyfrom about 1.5 to about 5. more preferably from about 2 to about 3.5.

DETAILED DESCRIPTION OF THE INVENTION I. FABRIC SOFTENING ACTIVE

Compositions of the present invention contain as an essential componentfrom about 2% to about 80%, preferably from about 13% to about 75%, morepreferably from about 17% to about 70%, and even more preferably fromabout 19% to about 65% by weight of the composition, of a fabricsoftener active selected from the compounds identified hereinafter, andmixtures thereof.

Fabric softeners that can be used herein are disclosed, at leastgenerically for the basic structures, in U.S. Pat. No. 3,861,870.Edwards and Diehl; U.S. Pat. No. 4,308,151, Cambre; U.S. Pat. No.3,886,075, Bernardino; U.S. Pat. No. 4,233,164, Davis; U.S. Pat. No.4,401,578, Verbruggen; U.S. Pat. No. 3,974,076, Wiersema and Rieke; andU.S. Pat. No. 4,237,016, Rudkin, Clint, and Young, all of said patentsbeing incorporated herein by reference.

Preferred fabric softening agents are disclosed in U.S. Pat. No.4,661,269, issued Apr. 28, 1987, in the names of Toan Trinh, Errol H.Wahl, Donald M. Swartley and Ronald L. Hemingway, said patent beingincorporated herein by reference.

The primary softener actives herein are those that are highlyunsaturated versions of the traditional softener actives, i.e., di-longchain alkyl nitrogen derivatives, normally cationic materials, such asdioleyldimethylammonium chloride and imidazolinium compounds asdescribed hereinafter. As discussed in more detail hereinafter, morebiodegradable fabric softener compounds can be present.

Examples of such fabric softeners can be found in U.S. Pat. No.3,408,361, Mannheimer, issued Oct. 29, 1968; U.S. Pat. No. 4,709,045,Kubo et al., issued Nov. 24, 1987; U.S. Pat. No. 4,233,451, Pracht etal., issued Nov. 11, 1980; U.S. Pat. No. 4,127,489, Pracht et al.,issued Nov. 28, 1979; U.S. Pat. No. 3,689,424, Berg et al., issued Sep.5, 1972; U.S. Pat. No. 4,128,485, Baumann et al., issued Dec. 5, 1978;U.S. Pat. No. 4,161,604, Elster et al., issued Jul. 17, 1979; U.S. Pat.No. 4,189,593, Wechsler et al., issued Feb. 19, 1980; and U.S. Pat. No.4,339,391, Hoffman et al., issued Jul. 13, 1982, said patents beingincorporated herein by reference.

Preferred fabric softeners of the invention comprise a majority ofcompounds as follows:

(1) softener having the formula:

 R_(4−m)−N⁽⁺⁾−R¹ _(m)A⁻

wherein each m is 2 or 3, each R¹ is a C₆-C₂₂, preferably C₁₄-C₂₀, butno more than one being less than about C₁₂ and then the other is atleast about 16, hydrocarbyl, or substituted hydrocarbyl substituent,preferably C₁₀-C₂₀ alkyl or alkenyl (unsaturated alkyl, includingpolyunsaturated alkyl, also referred to sometimes as “alkylene”). mostpreferably C₁₂-C₁₈ alkyl or alkenyl, and where the Iodine Value of afatty acid containing this R¹ group is from about 70 to about 140, morepreferably from about 80 to about 130; and most preferably from about 90to about 115 with a cis/trans ratio of from about 1:1 to about 50:1, theminimum being 1:1, preferably from about 2:1 to about 40:1, morepreferably from about 3:1 to about 30:1, and even more preferably fromabout 4:1 to about 20:1, and the total level of active containingpolyunsaturated fatty acyl groups (TPU) be typically from about 3% toabout 30%; each R¹ can also preferably be a branched chain C₁₄-C₂₂ alkylgroup, preferably a branched chain C₁₆-C₁₈ group; each R is H or a shortchain C₁-C₆, preferably C₁-C₃ alkyl or hydroxyalkyl group, e.g., methyl(most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl, or(R²O)₂₋₄H; and A⁻ is a softener compatible anion, preferably, chloride,bromide, methylsulfate, ethylsulfate, sulfate, and nitrate, morepreferably chloride and methyl sulfate;

(2) softener having the formula:

 wherein each R, R¹, and A⁻ have the definitions given above; each R² isa C₁₋₆ alkylene group, preferably an ethylene group; and G is an oxygenatom or an —NR— group;

(3) softener having the formula:

 wherein R¹, R² and G are defined as above;

 (4) reaction products of substantially unsaturated and/or branchedchain higher fatty acids with dialkylenetriamines in, e.g., a molecularratio of about 2:1, said reaction products containing compounds of theformula:

R¹—C(O)—NH—R²—NH—R³—NH—C(O)—R¹

 wherein R¹, R² are defined as above, and each R³ is a C₁₋₆ alkylenegroup, preferably an ethylene group;

(5) softener having the formula:

[R¹—C(O)—NR—R²—N(R) ₂—R³—NR—C(O)—R¹]⁺A⁻

 wherein R, R¹, R², R³ and A⁻ are defined as above;

(6) the reaction product of substantially unsaturated and/or branchedchain higher fatty acid with hydroxyalkylalkylenediamines in a molecularratio of about 2:1, said reaction products containing compounds of theformula:

R¹—C(O)—NH—R²—N(R³OH)—C(O)—R¹

 wherein R¹, R² and R³ are defined as above;

(7) softener having the formula:

 wherein R, R¹, R², and A⁻ are defined as above; and

(8) mixtures thereof.

Examples of Compound (1) are dialkylenedimethylammonium salts such asdicanoladimethylammonium chloride, dicanoladimethylammoniummethylsulfate, di(partially hydrogenated soybean, cis/trans ratio ofabout 4:1)dimethylammonium chloride, dioleyldimethylammonium chloride.Dioleyldimethylammonium chloride and di(canola)dimethylammonium chlorideare preferred. An example of commercially availabledialkylenedimethylammonium salts usable in the present invention isdioleyldimethylammonium chloride available from Witco Corporation underthe trade name Adogen® 472.

An example of Compound (2) is1-methyl-1-oleylamidoethyl-2-oleylimidazolinium methylsulfate wherein R¹is an acyclic aliphatic C₁₅-C₁₇ hydrocarbon group, R² is an ethylenegroup, G is a NH group, R⁵ is a methyl group and A⁻ is a methyl sulfateanion, available commercially from the Witco Corporation under the tradename Varisoft® 3690.

An example of Compound (3) is 1-oleylamidoethyl-2-oleylimidazolinewherein R¹ is an acyclic aliphatic C₁₅-C₁₇ hydrocarbon group, R² is anethylene group, and G is a NH group.

An example of Compound (4) is reaction products of oleic acids withdiethylenetriamine in a molecular ratio of about 2:1, said reactionproduct mixture containing N,N″-dioleoyldiethylenetriamine with theformula:

R¹—C(O)—NH—CH₂CH₂—NH—CH₂CH₂—NH—C(O)—R¹

wherein R¹—C(O) is oleoyl group of a commercially available oleic acidderived from a vegetable or animal source, such as Emersol® 223LL orEmersol® 7021, available from Henkel Corporation, and R² and R³ aredivalent ethylene groups.

An example of Compound (5) is a difatty amidoamine based softener havingthe formula:

[R¹—C(O)—NH—CH₂CH₂—N(CH₃) (CH₂CH₂OH)—CH₂CH₂—NH—C(O)—R¹]⁺CH₃SO₄ ⁻

wherein R¹—C(O) is oleoyl group, available commercially from the WitcoCorporation under the trade name Varisoft® 222LT.

An example of Compound (6) is reaction products of oleic acids withN-2-hydroxyethylethylenediamine in a molecular ratio of about 2:1, saidreaction product mixture containing a compound of the formula:

R¹—C(O)—NH—CH₂CH₂—N(CH₂CH₂OH)—C(O)—R¹

wherein R¹—C(O) is oleoyl group of a commercially available oleic acidderived from a vegetable or animal source, such as Emersol® 223LL orEmersol® 7021, available from Henkel Corporation.

An example of Compound (7) is the diquaternary compound having theformula:

wherein R¹ is derived from oleic acid, and the compound is availablefrom Witco Company.

The above individual Compounds (actives) can be used individually or asmixtures.

One type of optional but highly desirable cationic compound which can beused in combination with the above softener actives are compoundscontaining one long chain acyclic C₈-C₂₂ hydrocarbon group, selectedfrom the group consisting of:

wherein R⁷ is hydrogen or a C₁-C₄ saturated alkyl or hydroxyalkyl group,and R¹ and A⁻ are defined as herein above;

(9) acyclic quaternary ammonium salts having the formula:

[R¹—N(R⁵)₂—R⁶]⁺A⁻

 wherein R⁵ and R⁶ are C₁-C₄ alkyl or hydroxyalkyl groups, and R¹ and A⁻are defined as herein above;

(10) substituted imidazolinium salts having the formula:

 wherein R⁷ is hydrogen or a C₁-C₄ saturated alkyl or hydroxyalkylgroup, and R¹ and A⁻ are defined as hereinabove;

(11) substituted imidazolinium salts having the formula:

 wherein R⁵ is a C₁-C₄ alkyl or hydroxyalkyl group, and R¹, R², and A⁻are as defined above;

(12) alkylpyridiniun salts having the formula:

 wherein R⁴ is an acyclic aliphatic C₈-C₂₂ hydrocarbon group and A⁻ isan anion; and

(13) alkanamide alkylene pyridinium salts having the formula:

wherein R¹, R² and A⁻ are defined as herein above; and mixtures thereof.

Examples of Compound (9) are the monoalkenyltrimethylammonium salts suchas monooleyltrimethylammonium chloride, monocanolatrimethylammoniumchloride, and soyatrimethylammonium chloride. Monooleyltrimethylammoniumchloride and monocanolatrimethylammonium chloride are preferred. Otherexamples of Compound (9) are soyatrimethylammoniuin chloride availablefrom Witco Corporation under the trade name Adogen® 415,erucyltrimethylammonium chloride wherein R¹ is a C₂₂ hydrocarbon groupderived from a natural source; soyadimethylethylammonium ethylsulfatewherein R¹ is a C₁₆-C₁₈ hydrocarbon group, R⁵ is a methyl group, R⁶ isan ethyl group, and A⁻ is an ethylsulfate anion; and methylbis(2-hydroxyethyl)oleylammonium chloride wherein R¹ is a C₁₈hydrocarbon group, R⁵ is a 2-hydroxyethyl group and R⁶ is a methylgroup.

An example of Compound (1) is1-ethyl-1-(2-hydroxyethyl)-2-isoheptadecylimidazolinium ethylsulfatewherein R¹ is a C₁₇ hydrocarbon group, R² is an ethylene group, R⁵ is anethyl group, and A⁻ is an ethylsulfate anion.

Anion A

In the cationic nitrogenous salts herein, the anion A⁻, which is anysoftener compatible anion, provides electrical neutrality. Most often,the anion used to provide electrical neutrality in these salts is from astrong acid, especially a halide, such as chloride, bromide, or iodide.However, other anions can be used, such as methylsulfate, ethylsulfate,acetate, formate, sulfate, carbonate, and the like. Chloride andmethylsulfate are preferred herein as anion A.

As mentioned before, the softener active can also comprise a smallamount of more biodegradable fabric softener active, especially:

(A) Diester Quaternary Ammonium Fabric Softening Active Compound (DEOA)

(1) The first type of DEQA preferably comprises, as the principalactive, compounds of the formula

[(R)_(4−m)−N⁺−[(CH₂)_(n)−Y−R¹]_(m)]A⁻

wherein: each R and A⁻ are as defined hereinbefore; each m is 2 or 3;each n is from 1 to about 4, preferably 2; each Y is —O—(O)C—,—(R)N—(O)C—, —C(O)—N(R)—, or —C(O)—O—, preferably —O(O)C—, but not—C(O)O—; the sum of carbons in each R¹, plus one when Y is —O—(O)C— or—(R)N—(O)C—, is C₆-C₂₂, preferably C₁₄-C₂₀, but no more than one YR¹ sumbeing less than about 12 and then the other YR¹ sum is at least about16, with each R¹ being a long chain C₈-C₂₂ (or C₇-C₂₁)hydrocarbyl, orsubstituted hydrocarbyl substituent, preferably C₁₀-C₂₀ (or C₉-C₁₉)alkyl or alkenyl, most preferably C₁₂-C₁₈ (or C₁₁-C₁₇) alkyl or alkenyl,and where, when said sum of carbons is C₁₆-C₁₈ and R¹ is a straightchain alkyl or alkenyl group, the Iodine Value (hereinafter referred toas IV) of the parent fatty acid of this R¹ group is preferably fromabout 20 to about 140, more preferably from about 50 to about 130; andmost preferably from about 70 to about 115.

As before, the counterion, A⁻ above, can be any softener-compatibleanion, preferably the anion of a strong acid, for example, chloride,bromide, methylsulfate, ethylsulfate, sulfate, nitrate and the like,more preferably chloride. The anion can also, but less preferably, carrya double charge in which case A⁻ represents half a group.

Preferred cationic, preferably biodegradable quaternary, ammonium fabricsoftening compounds can contain the group —(O)CR¹ which is derived fromanimal fats, unsaturated, and polyunsaturated, fatty acids, e.g., oleicacid, and/or partially hydrogenated fatty acids, derived from vegetableoils and/or partially hydrogenated vegetable oils, such as, canola oil,safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, talloil, rice bran oil, etc. Non-limiting examples of fatty acids (FA) havethe following approximate distributions:

Fatty Acyl Group FA¹ FA² FA³ FA⁴ FA⁵ C12 trace trace 0 0 0 C14 3 3 0 0 0C16 4 4 5 5 5 C18 0 0 5 6 6 C14:1 3 3 0 0 0 C16:1 11 7 0 0 3 C18:1 74 7371 68 67 C18:2 4 8 8 11 11 C18:3 0 1 1 2 2 C20:1 0 0 2 2 2 C20 and up 00 2 0 0 Unknowns 0 0 6 6 7 Total 99 99 100 100 102 IV 86-90 88-95 99 10095 cis/trans (C18:1) 20-30 20-30 4 5 5 TPU 4 9 10 13 13 TPU is thepercentage of polyunsaturates present.

Mixtures of fatty acids, and mixtures of FAs that are derived fromdifferent fatty acids can be used, and are preferred. Nonlimitingexamples of FA's that can be blended, to form FA's of this invention areas follows:

Fatty Acyl Group FA⁶ FA⁷ C14 0 1 C16 11 25 C18 4 20 C14:1 0 0 C16:1 1 0C18:1 27 45 C18:2 50 6 C18:3 7 0 Unknowns 0 3 Total 100 100 IV 125-13856 cis/trans (C18:1) Not Available 7 TPU 57 6

FA⁶ is prepared from a soy bean fatty acid, and FA⁷ is pre pared from aslightly hydrogenated tallow fatty acid.

Also, optionally, the fatty acids can be replaced, where appropriate, bythe corresponding alkylene groups. The R¹ groups can also comprisebranched chains, e.g., from isostearic acid, for at least part of the R¹groups. The total of active represented by the branched chain groups,when they are present, is typically from about 1% to about 100%,preferably from about 10% to about 70%, more preferably from about 20%to about 50%.

Fatty Acyl Group FA⁸ FA⁹ FA¹⁰ Isomyristic acid — 1-2 — Myristic acid 7-11 0.5-1   — Isopalmitic acid 6-7 6-7 1-3 Palmitic acid 4-5 6-7 —Isostearic acid 70-76 80-82 60-66 Stearic acid — 2-3  8-10 Isoleic acid— — 13-17 Oleic acid — —  6-12 IV 3 2  7-12

FA⁸-FA¹⁰ are prepared from different commercially available isostearicacids.

The more preferred softener actives, especially DEQA's, are those thatare prepared as a single DEQA from blends of all the different fattyacids that are represented (total fatty acid blend), rather than fromblends of mixtures of separate finished DEQA's that are prepared fromdifferent portions of the total fatty acid blend.

It is preferred that at least a majority of the fatty acyl, or alkyl,groups are unsaturated, e.g., from about 50% to 100%, preferably fromabout 55% to about 95%, more preferably from about 60% to about 90%, andthat the total level of active containing polyunsaturated fatty acylgroups (TPU) be preferably from about 3% to about 30%. The cis/transratio for the unsaturated fatty acyl groups is usually important, withthe cis/trans ratio being from 1:1 to about 50:1, the minimum being 1:1,preferably at least 3:1, and more preferably from about 4:1 to about20:1. (As used herein, the “percent of softener active” containing agiven R¹ group is the same as the percentage of that same R¹ group is tothe total R¹ groups used to form all of the softener actives.)

The unsaturated, including the preferred polyunsaturated, fatty acyland/or alkylene groups, discussed hereinbefore and hereinafter,surprisingly provide effective softening, but also provide betterrewetting characteristics, good antistatic characteristics, andespecially, superior recovery after freezing and thawing.

The highly unsaturated materials are also easier to formulate intoconcentrated premixes that maintain their low viscosity and aretherefore easier to process, e.g., pump, mixing, etc. These highlyunsaturated materials (total level of active containing polyunsaturatedfatty acyl groups (TPU) being typically from about 3% to about 30%, withonly the low amount of solvent that normally is associated with suchmaterials, i.e., from about 5% to about 20%, preferably from about 8% toabout 25%, more preferably from about 10% to about 20%, weight of thetotal softener/solvent mixture, are also easier to formulate intoconcentrated, stable compositions of the present invention, even atambient temperatures. This ability to process the actives at lowtemperatures is especially important for the polyunsaturated groups,since it mimimizes degradation. Additional protection againstdegradation can be provided when the compounds and softener compositionscontain effective antioxidants, chelants, and/or reducing agents, asdisclosed hereinafter.

The present invention can contain medium-chain cationic ammonium fabricsoftening compound, including DEQAs having the above formula (1) and/orformula (2), below, wherein:

each Y is —O—(O)C—, —(R)N—(O)C—, —C(O)—N(R)—, or —C(O)—O—, preferably—O—(O)C—;

m is 2 or 3, preferably 2;

each n is 1 to 4, preferably 2;

each R is as defined hereinbefore;

each R¹, or YR¹ hydrophobic group is a saturated, C₈-C₁₄, preferably aC₁₂₋₁₄ hydrocarbyl, or substituted hydrocarbyl substituent (the IV ispreferably about 10 or less, more preferably less than about 5), [Thesum of the carbons in the hydrophobic group is the number of carbonatoms in the R¹ group, or in the YR¹ group when Y is——O—(O)C— or—(R)N—(O)C—] and the counterion, A⁻, is the same as above. Preferably A⁻does not include phosphate salts.

The saturated C₈-C₁₄ fatty acyl groups can be pure derivatives or can bemixed chainlengths.

Suitable fatty acid sources for said fatty acyl groups are coco, lauric,caprylic, and capric acids.

For C₁₂-C₁₄ (or C₁₁-C₁₃) hydrocarbyl groups, the groups are preferablysaturated, e.g., the IV is preferably less than about 10, preferablyless than about 5.

It will be understood that substituents R and R¹ can optionally besubstituted with various groups such as alkoxyl or hydroxyl groups, andcan be straight, or branched so long as the R¹ groups maintain theirbasically hydrophobic character.

A preferred long chain DEQA is the DEQA prepared from sources containinghigh levels of polyunsaturation, i.e.,N,N-di(acyl-oxyethyl)-N,N-dimethyl ammonium chloride, where the acyl isderived from fatty acids containing sufficient polyunsaturation, e.g.,mixtures of tallow fatty acids and soybean fatty acids. Anotherpreferred long chain DEQA is the dioleyl (nominally) DEQA, i.e., DEQA inwhich N,N-di(oleoyl-oxyethyl)-N,N-dimethyl ammonium chloride is themajor ingredient. Preferred sources of fatty acids for such DEQAs arevegetable oils, and/or partially hydrogenated vegetable oils, with highcontents of unsaturated, e.g., oleoyl groups.

As used herein, when the DEQA diester is specified, it can include themonoester that is present. Preferably, at least about 80% of the DEQA isin the diester form, and from 0% to about 20% can be DEQA monoester,e.g., one YR¹ group is either OH, or —C(O)OH, and, for Formula 1, m is2. The corresponding diamide and/or mixed ester-anide can also includethe active with one long chain hydrophobic group, e.g., one YR¹ group iseither —N(R)H , or —C(O)OH. In the following, any disclosure, e.g.,levels, for the monoester actives is also applicable to the monoamideactives. For softening, under no/low detergent carry-over laundryconditions the percentage of monoester should be as low as possible,preferably no more than about 5%. However, under high, anionic detergentsurfactant or detergent builder carry-over conditions, some monoestercan be preferred. The overall ratios of diester to monoester are fromabout 100:1 to about 2:1, preferably from about 50:1 to about 5:1, morepreferably from about 13:1 to about 8:1. Under high detergent carry-overconditions, the di/monoester ratio is preferably about 11:1. The levelof monoester present can be controlled in manufacturing the DEQA.

The above compounds, used as the biodegradable quatemized ester-aminesoftening material in the practice of this invention, can be preparedusing standard reaction chemistry. In one synthesis of a di-estervariation of DTDMAC, an amine of the formula RN(CH₂CH₂OH)₂ where R ise.g., alkyl, is esterified at both hydroxyl groups with an acid chlorideof the formula R¹C(O)Cl, to form an amine which can be made cationic byacidification (one R is H) to be one type of softener, or thenquatemized with an alkyl halide, RX, to yield the desired reactionproduct (wherein R and R¹ are as defined hereinbefore). However, it willbe appreciated by those skilled in the chemical arts that this reactionsequence allows a broad selection of agents to be prepared.

Yet another DEQA softener active that is suitable for the formulation ofthe concentrated, clear liquid fabric softener compositions of thepresent invention has the above formula (1) wherein one R group is aC₁₋₄ hydroxy alkyl group, preferably one wherein one R group is ahydroxyethyl group. An example of such a hydroxyethyl ester active isdi(acyloxyethyl)(2-hydroxyethyl)methyl ammonium methyl sulfate, whereinthe acyl group is derived from FA¹ described herein before.

(2) The second type of DEQA active has the general formula:

R₃—N⁺—CH₂—CH(YR¹)—CH₂—YR¹A⁻

wherein each Y, R, R¹, and A⁻ have the same meanings as before. Suchcompounds include those having the formula:

[CH₃]₃N⁽⁺⁾[CH₂CH(CH₂O(O)CR¹)O(O)CR¹]Cl⁽⁻⁾

where each R is a methyl or ethyl group and preferably each R¹ is in therange of C₁₅ to C₁₉. Degrees of branching and substitution can bepresent in the alkyl or alkenyl chains. The anion X⁽⁻⁾ in the moleculeis the same as in DEQA (1) above. As used herein, when the diester isspecified, it can include the monoester that is present. The amount ofmonoester that can be present is the same as in DEQA (1). An example ofa preferred DEQA of formula (2) is the “propyl” ester quaternaryammoniun fabric softener active having the formula1,2-di(acyloxy)-3-trimethylammoniopropane chloride, wherein the acylgroup is the same as that of FA⁵.

These types of agents and general methods of making them are disclosedin U.S. Pat. No. 4,137,180, Naik et al., issued Jan. 30, 1979, which isincorporated herein by reference.

In preferred DEQA softener actives (1) and (2), each R¹ is ahydrocarbyl, or substituted hydrocarbyl, group, preferably, alkyl,monounsaturated alkenyl, and polyunsaturated alkenyl groups, with thesoftener active containing polyunsaturated alkenyl groups beingpreferably at least about 3%, more preferably at least about 5%, morepreferably at least about 10%, and even more preferably at least about15%, by weight of the total softener active present; the activespreferably containing mixtures of R¹ groups, especially within theindividual molecules, and also, optionally, but preferably, thesaturated R¹ groups comprising branched chains, e.g., from isostearicacid, for at least part of the saturated R¹ groups, the total of activerepresented by the branched chain groups preferably being from about 1%to about 90%, preferably from about 10% to about 70%, more preferablyfrom about 20% to about 50%.

[In preferred quaternary ammonium fabric softening compounds, andespecially in the DEQAs, —(O)CR¹ is derived from unsaturated fatty acid,e.g., oleic acid, and/or fatty acids and/or partially hydrogenated fattyacids, derived from animal fats, vegetable oils and/or partiallyhydrogenated vegetable oils, such as: canola oil; safflower oil; peanutoil; sunflower oil; soybean oil; corn oil; tall oil; rice bran oil;etc.] [As used herein, similar biodegradable fabric softener activescontaining ester linkages are referred to as “DEQA”, which includes bothdiester, triester, and monoester compounds containing from one to three,preferably two, long chain hydrophobic groups. The corresponding amidesoftener actives and the mixed ester-amide softener actives can alsocontain from one to three, preferably two, long chain hydrophobicgroups. These fabric softener actives have the characteristic that theycan be processed by conventional mixing means at ambient temperature, atleast in the presence of about 15% of solvent C. as disclosedhereinbefore.]

The DEQAs herein can also contain a low level of fatty acid, which canbe from unreacted starting material used to form the DEQA and/or as aby-product of any partial degradation (hydrolysis) of the softeneractive in the finished composition. It is preferred that the level offree fatty acid be low, preferably below about 10%, and more preferablybelow about 5%, by weight of the softener active.

Preferred Process for Preparing Softener Actives

The fabric softener actives of the present invention are preferablyprepared by a process wherein a chelant, preferably adiethylenetriaminepentaacetate (DTPA) and/or an ethylenediamine-N,N′-disuccinate (EDDS) is added to the process. The resultingsoftener active has reduced discoloration and malodor associatedtherewith. The typical process comprises the steps of:

a) providing a source of triglyceride and reacting the source oftriglyceride to form a mixture of fatty acids and/or fatty acid esters;

b) using the mixture formed from step (a) to react:

(1) under either amidification conditions, or conditions to form animidazoline, with one or more amines of the formula R₂—N—R²—NR—R²—NR₂wherein R is hydrogen or a short chain C₁-C₆ alkyl or hydroxyalkylgroup, benzyl or mixtures thereof, more preferably a C₁-C₃ alkyl, mostpreferably a methyl, ethyl, propyl, or hydroxyethyl, with at least one Ron each terminal nitrogen being hydrogen, and wherein R² is an alkylenegroup containing from one to four carbon atoms, to form a mixture offatty acid amides; or

(2) with ammonia at elevated temperature to form a fatty amide followedby further reaction to produce a nitrile and the evolution of water, thenitrile then is reduced with hydrogen to a primary amine under heat,pressure and catalyst and further reaction converts the primary amineinto the desired difatty secondary amine;

c) quaternizing, if desired, the mixture of fatty acid amides, orimidazolines, formed from step (b) (1) by reacting the mixture underquaternizing conditions with a quaternizing agent of the formula RXwherein R is defined as in step (b) and X is a softener compatibleanion, preferably selected from the group consisting of chloride,bromide, methylsulfate, ethylsulfate, sulfate, and nitrate therebyforming a quaternary fabric softener active, wherein at least step (c)is carried out in the presence of a chelating agent selected from thegroup consisting of diethylenetriaminepentaacetic acid,ethylenediamine-N,N′-disuccinnic acid and mixtures thereof; or

for (b) (2), if the chloride quaternary is desired, the secondary amineis methylated with methyl chloride in the presence of caustic to formthe dialkyl dimethyl ammonium chloride as disclosed below, oralternatively, if the methyl sulfate quatemary is desired, then thesecondary amine is converted to a methyl tertiary amine by reaction withformalin and hydrogen in the presence of a catalyst and the resultingmethyl amine is then quaternized with methyl chloride or dimethylsulfate.

The step of reacting the source of triglyceride can further includereacting in the presence of the chelating agent step (b) can furtherinclude the presence of the chelating agent.

The total amount of added chelating agent is preferably within the rangeof from about 10 ppm to about 5,000 ppm, more preferably within therange of from about 100 ppm to about 2500 ppm by weight of the formedsoftener active. The source of triglyceride is preferably selected fromthe group consisting of animal fats, vegetable oils, partiallyhydrogenated vegetable oils, and mixtures thereof. More preferably, thevegetable oil or partially hydrogenated vegetable oil is selected fromthe group consisting of canola oil, partially hydrogenated canola oil,safflower oil, partially hydrogenated safflower oil, peanut oil,partially hydrogenated peanut oil, sunflower oil, partially hydrogenatedsunflower oil, corn oil, partially hydrogenated corn oil, soybean oil,partially hydrogenated soybean oil, tall oil, partially hydrogenatedtall oil, rice bran oil, partially hydrogenated rice bran oil, andmixtures thereof. Most preferably, the source of triglyceride is canolaoil, partially hydrogenated canola oil, and mixtures thereof. Theprocess can also include the step of adding from about 0.01% to about 2%by weight of the composition of an antioxidant compound to any or all ofsteps (a), (b) or (c). The products of the above process are newmaterials.

The present invention also includes a process for the preparation of afabric softening premix composition. This method comprises preparing afabric softening active as described above and mixing the fabricsoftener active, optionally containing a low molecular weight solventwith a principal solvent having a ClogP of from about 0.15 to about 0.64thereby forming a fabric softener premix. The premix can comprise fromabout 55% to about 85% by weight of fabric softening active and fromabout 10% to about 30% by weight of a principal solvent. The process canfurther comprise the step of adding a low molecular weight water solublesolvent selected from the group consisting of: ethanol, isopropanol,propylene glycol, 1,3-propanediol, propylene carbonate, hexylene glycoland mixtures thereof to the premix. Again, the process can also includethe step of adding from about 0.01% to about 2% by weight of thecomposition of an antioxidant compound to any or all of steps (a), (b)or (c). The products of the above process are also new compositions.

A process for preparing a fabric softening composition comprises thesteps of forming a premix as described above and the steps of forming awater seat by combining water and a mineral acid; and mixing the premixand the water seat with agitation to form a fabric softeningcomposition. The process can further comprise one or more steps,including the steps of adjusting the viscosity of the fabric softeningcomposition with the addition of a solution of calcium chloride, addinga chelating agent to the water seat and adding a perfume ingredient tothe premix, or, preferably, the finished product. The products of theabove process are also new compositions.

The above processes produce a fabric softener active with reducedcoloration and malodor.

II. PRINCIPAL SOLVENT SYSTEM

The compositions of the present invention comprise less than about 40%,preferably from about 10% to about 35%, more preferably from about 12%to about 25%, and even more preferably from about 14% to about 20%, ofthe principal solvent, by weight of the composition. Said principalsolvent is selected to minimize solvent odor impact in the compositionand to provide a low viscosity to the final composition. For example,isopropyl alcohol is not very effective and has a strong odor. n-Propylalcohol is more effective, but also has a distinct odor. Several butylalcohols also have odors but can be used for effectiveclarity/stability, especially when used as part of a principal solventsystem to minimize their odor.

The alcohols are also selected for optimum low temperature stability,that is they are able to form compositions that are liquid withacceptable low viscosities and translucent, preferably clear, down toabout 40° F. (about 4.4° C.) and are able to recover after storage downto about 20° F. (about 6.7° C.).

The suitability of any principal solvent for the formulation of theliquid, concentrated, preferably clear, fabric softener compositionsherein with the requisite stability is surprisingly selective. Suitablesolvents can be selected based upon their octanol/water partitioncoefficient (P). Octanol/water partition coefficient of a principalsolvent is the ratio between its equilibrium concentration in octanoland in water. The partition coefficients of the principal solventingredients of this invention are conveniently given in the form oftheir logarithm to the base 10, logP.

The logP of many ingredients has been reported; for example, thePomona92 database, available from Daylight Chemical Information Systems,Inc. (Daylight CIS), Irvine, Calif., contains many, along with citationsto the original literature. However, the logP values are mostconveniently calculated by the “CLOGP” program, also available fromDaylight CIS. This program also lists experimental logP values when theyare available in the Pomona92 database. The “calculated logP” (ClogP) isdetermined by the fragment approach of Hansch and Leo (cf, A. Leo, inComprehensive Medicinal Chemistry, Vol. 4, C. Hansch, P. G. Sammens, J.B. Taylor and C. A. Ramsden, Eds., p. 295, Pergamnon Press, 1990,incorporated herein by reference). The fragment approach is based on thechemical structure of each ingredient, and takes into account thenumbers and types of atoms, the atom connectivity, and chemical bonding.The ClogP values, which are the most reliable and widely used estimatesfor this physicochemical property, are preferably used instead of theexperimental logP values in the selection of the principal solventingredients which are useful in the present invention. Other methodsthat can be used to compute ClogP include, e.g., Crippen's fragmentationmethod as disclosed in J. Chem. Inf. Comput. Sci., 27, 21 (1987);Viswanadhan's fragmentation method as disclose in J. Chem. Inf. Comput.Sci., 29, 163 (1989); and Broto's method as disclosed in Eur. J. Med.Chem.—Chim. Theor., 19, 71 (1984).

The principal solvents herein are selected from those having a ClogP offrom about 0.15 to about 0.64, preferably from about 0.25 to about 0.62,and more preferably from about 0.40 to about 0.60, said principalsolvent preferably being asymmetric, and preferably having a melting, orsolidification, point that allows it to be liquid at, or near roomtemperature. Solvents that have a low molecular weight and arebiodegradable are also desirable for some purposes. The more asymmetricsolvents appear to be very desirable, whereas the highly symmetricalsolvents, having a center of synmmetry, such as 1,7-heptanediol, or1,4-bis(hydroxymethyl)cyclohexane, appear to be unable to provide theessentially clear compositions when used alone, even though their ClogPvalues fall in the preferred range. One can select the most suitableprincipal solvent by determining whether a composition containing about27% di(oleyoyloxyethyl)dimethylammonium chloride, about 16-20% ofprincipal solvent, and about 4-6% ethanol remains clear during storageat about 40° F. (about 4.4° C.) and recovers from being frozen at about0° F. (about −18° C.).

The most preferred principal solvents can be identified by theappearance of the freeze-dried dilute treatment compositions used totreat fabrics. These dilute compositions appear to have dispersions offabric softener that exhibit a more uni-lamellar appearance thanconventional fabric softener compositions. The closer to uni-lamellarthe appearance, the better the compositions seem to perform. Thesecompositions provide surprisingly good fabric softening as compared tosimilar compositions prepared in the conventional way with the samefabric softener active. The compositions also inherently provideimproved perfume deposition as compared to conventional fabric softeningcompositions, especially when the perfume is added to the compositionsat, or near, room temperature.

Operable principal solvents are listed below under various listings,e.g., aliphatic and/or alicyclic diols with a given number of carbonatoms; monols; derivatives of glycerine; alkoxylates of diols; andmixtures of all of the above. The preferred principal solvents are initalics and the most preferred principal solvents are in bold type. Thereference numbers are the Chemical Abstracts Service Registry numbers(CAS No.) for those compounds that have such a number. Novel compoundshave a method identified, described hereinafter, that can be used toprepare the compounds. Some inoperable principal solvents are alsolisted below for comparison purposes. The inoperable principal solvents,however, can be used in mixtures with operable principal solvents.Operable principal solvents can be used to make concentrated fabricsoftener compositions that meet the stability/clarity requirements setforth herein.

Many diol principal solvents that have the same chemical formula canexist as many stereoisomers and/or optical isomers. Each isomer isnormally assigned with a different CAS No. For examples, differentisomers of 4-methyl-2,3-hexanediol are assigned to at least thefollowing CAS Nos: 146452-51-9; 146452-50-8; 146452-49-5; 146452-48-4;123807-34-1; 123807-33-0; 123807-32-9; and 123807-31-8.

In the following listings, for simplicity, each chemical formula islisted with only one CAS No. This disclosure is only for exemplificationand is sufficient to allow the practice of the invention. The disclosureis not limiting. Therefore, it is understood that other isomers withother CAS Nos, and their mixtures, are also included. By the same token,when a CAS No. represents a molecule which contains some particularisotopes, e.g., deuterium, tritium, carbon-13, etc., it is understoodthat materials which contain naturally distributed isotopes are alsoincluded, and vice versa. The methods disclosed for making the solventsare described fuilly in the copending application, Ser. No. 08/679,694,filed Jul. 11, 1996 in the names of E. H. Wahl, T. Trinh, E. P.Gosselink, J. C. Letton, and M. R. Sivik, for Fabric SofteningCompound/Composition, said application being incorporated herein byreference.

TABLE I MONO-OLS CAS No. n-propanol 71-23-8 2-butanol 15892-23-62-methyl-2-propanol 75-65-0

TABLE II C6 DIOLS Operable Isomers CAS No. 2,3-butanediol, 2,3-dimethyl-76-09-5 1,2-butanediol, 2,3-dimethyl- 66553-15-9 1,2-butanediol,3,3-dimethyl- 59562-82-2 2,3-pentanediol, 2-methyl- 7795-80-42,3-pentanediol, 3-methyl- 63521-37-9 2,3-pentanediol, 4-methyl-7795-79-1 2,3-hexanediol 617-30-1 3,4-hexanediol 922-17-81,2-butanediol, 2-ethyl- 66553-16-0 1,2-pentanediol, 2-methyl-20667-05-4 1,2-pentanediol, 3-methyl- 159623-53-7 1,2-pentanediol,4-methyl- 72110-08-8 1,2-hexanediol 6920-22-5

TABLE III C7 DIOLS Operable Isomers CAS No. 1,3-propanediol, 2-butyl-2612-26-2 1,3-propanediol, 2,2-diethyl- 115-76-4 1,3-propanediol,2-(1-methylpropyl)- 33673-01-7 1,3-propanediol, 2-(2-methylpropyl)-26462-20-3 1,3-propanediol, 2-methyl-2-propyl- 73-26-2 1,2-butanediol,2,3,3-trimethyl- Method B 1,4-butanediol, 2-ethyl-2-methyl- 76651-98-41,4-butanediol, 2-ethyl-3-methyl- 66225-34-1 1,4-butanediol, 2-propyl-62946-68-3 1,4-butanediol, 2-isopropyl- 39497-66-0 1,5-pentanediol,2,2-dimethyl- 3121-82-2 1,5-pentanediol, 2,3-dimethyl- 81554-20-31,5-pentanediol, 2,4-dimethyl- 2121-69-9 1,5-pentanediol, 3,3-dimethyl-53120-74-4 2,3-pentanediol, 2,3-dimethyl- 6931-70-0 2,3-pentanediol,2,4-dimethyl- 66225-53-4 2,3-pentanediol, 3,4-dimethyl- 37164-04-82,3-pentanediol, 4,4-dimethyl- 89851-45-6 3,4-pentanediol, 2,3-dimethyl-Method B 1,5-pentanediol, 2-ethyl- 14189-13-0 1,6-hexanediol, 2-methyl-25258-92-8 1,6-hexanediol, 3-methyl- 4089-71-8 2,3-hexanediol, 2-methyl-59215-55-3 2,3-hexanediol, 3-methyl- 139093-40-6 2,3-hexanediol,4-methyl- *** 2,3-hexanediol, 5-methyl- Method B 3,4-hexanediol,2-methyl- Method B 3,4-hexanediol, 3-methyl- 1893847-1 1,3-heptanediol23433-04-7 1,4-heptanediol 40646-07-9 1,5-heptanediol 60096-09-51,6-heptanediol 13175-27-4 Preferred Isomers 1,3-propanediol, 2-butyl-2612-26-2 1,4-butanediol, 2-propyl- 62946-68-3 1,5-pentanediol, 2-ethyl-14189-13-0 2,3-pentanediol, 2,3-dimethyl- 6931-70-0 2,3-pentanediol,2,4-dimethyl- 66225-53-4 2,3-pentanediol, 3,4-dimethyl- 37164-04-82,3-pentanediol, 4,4-dimethyl- 89851-45-6 3,4-pentanediol, 2,3-dimethyl-Method B 1,6-hexanediol, 2-methyl- 25258-92-8 1,6-hexanediol, 3-methyl-4089-71-8 1,3-heptanediol 23433-04-7 1,4-heptanediol 40646-07-91,5-heptanediol 60096-09-5 1,6-heptanediol 13175-27-4 More PreferredIsomers 2,3-pentanediol, 2,3-dimethyl- 6931-70-0 2,3-pentanediol,2,4-dimethyl- 66225-53-4 2,3-pentanediol, 3,4-dimethyl- 37164-04-82,3-pentanediol, 4,4-dimethyl- 89851-45-6 3,4-pentanediol, 2,3-dimethyl-Method B

and mixtures thereof.

TABLE IV OCTANEDIOL ISOMERS PROPANEDIOL DERIVATIVES Chemical Name CASNo. Operable Isomers 1,3-propanediol, 2-(2-methylbutyl)- 87194-40-91,3-propanediol, 2-(1,1-dimethylpropyl)- Method D 1,3-propanediol,2-(1,2-dimethylpropyl)- Method D 1,3-propanediol, 2-(1-ethylpropyl)-25462-28-6 1,3-propanediol, 2-(1-methylbutyl)- 22131-29-91,3-propanediol, 2-(2,2-dimethylpropyl)- Method D 1,3-propanediol,2-(3-methylbutyl)- 25462-27-5 1,3-propanediol, 2-butyl-2-methyl-3121-83-3 1,3-propanediol, 2-ethyl-2-isopropyl- 24765-55-71,3-propanediol, 2-ethyl-2-propyl- 25450-88-8 1,3-propanediol,2-methyl-2-(1-methylpropyl)- 813-60-5 1,3-propanediol,2-methyl-2-(2-methylpropyl)- 25462-42-4 1,3-propanediol,2-tertiary-butyl-2-methyl- 25462-45-7 More Preferred Isomers1,3-propanediol, 2-(1,1-dimethylpropyl)- Method D 1,3-propanediol,2-(1,2-dimethylpropyl)- Method D 1,3-propanediol, 2-(1-ethylpropyl)-25462-28-6 1,3-propanediol, 2-(2,2-dimethylpropyl)- Method D1,3-propanediol, 2-ethyl-2-isopropyl- 24765-55-7 1,3-propanediol,2-methyl-2-(1-methylpropyl)- 813-60-5 1,3-propanediol,2-methyl-2-(2-methylpropyl)- 25462-42-4 1,3-propanediol,2-tertiary-butyl-2-methyl- 25462-45-7 BUTANEDIOL DERIVATIVES OperableIsomers 1,3-butanediol, 2,2-diethyl- 99799-77-6 1,3-butanediol,2-(1-methylpropyl)- Method C 1,3-butanediol, 2-butyl- 83988-22-11,3-butanediol, 2-ethyl-2,3-dimethyl- Method D 1,3-butanediol,2-(1,1-dimethylethyl)- 67271-58-3 1,3-butanediol, 2-(2-methylpropyl)-Method C 1,3-butanediol, 2-methyl-2-isopropyl- Method C 1,3-butanediol,2-methyl-2-propyl- 99799-79-8 1,3-butanediol, 3-methyl-2-isopropyl-Method C 1,3-butanediol, 3-methyl-2-propyl- Method D 1,4-butanediol,2,2-diethyl- Method H 1,4-butanediol, 2-methyl-2-propyl- Method H1,4-butanediol, 2-(1-methylpropyl)- Method H 1,4-butanediol,2-ethyl-2,3-dimethyl- Method F 1,4-butanediol, 2-ethyl-3,3-dimethyl-Method F 1,4-butanediol, 2-(1,1-dimethylethyl)- 36976-70-21,4-butanediol, 2-(2-methylpropyl)- Method F 1,4-butanediol,2-methyl-3-propyl- 90951-76-1 1,4-butanediol, 3-methyl-2-isopropyl-99799-24-3 Preferred Isomers 1,3-butanediol, 2,2-diethyl- 99799-77-61,3-butanediol, 2-(1-methylpropyl)- Method C 1,3-butanediol, 2-butyl-83988-22-1 1,3-butanediol, 2-ethyl-2,3-dimethyl- Method D1,3-butanediol, 2-(1,1-dimethylethyl)- 67271-58-3 1,3-butanediol,2-(2-methylpropyl)- Method C 1,3-butanediol, 2-methyl-2-isopropyl MethodC 1,3-butanediol, 2-methyl-2-propyl- 99799-79-8 1,3-butanediol,3-methyl-2-propyl- Method D 1,4-butanediol, 2,2-diethyl- Method H1,4-butanediol, 2-ethyl-2,3-dimethyl- Method F 1,4-butanediol,2-ethyl-3,3-dimethyl- Method F 1,4-butanediol, 2-(1,1-dimethylethyl)-36976-70-2 1,4-butanediol, 3-methyl-2-isopropyl- 99799-24-3 MorePreferred Isomers 1,3-butanediol, 2-(1-methylpropyl)- Method C1,3-butanediol, 2-(2-methylpropyl)- Method C 1,3-butanediol, 2-butyl-83988-22-1 1,3-butanediol, 2-methyl-2-propyl- 99799-79-8 1,3-butanediol,3-methyl-2-propyl- Method D 1,4-butanediol, 2,2-diethyl- Method H1,4-butanediol, 2-ethyl-2,3-dimethyl- Method F 1,4-butanediol,2-ethyl-3,3-dimethyl- Method F 1,4-butanediol, 2-(1,1-dimethylethyl)-36976-70-2 TRIMETHYLPENTANEDIOL ISOMERS Operable Isomers1,3-pentanediol, 2,2,3-trimethyl- 35512-54-0 1,3-pentanediol,2,2,4-trimethyl- 144-19-4 1,3-pentanediol, 2,3,4-trimethyl- 116614-13-21,3-pentanediol, 2,4,4-trimethyl- 109387-36-2 1,3-pentanediol,3,4,4-trimethyl- 81756-50-5 1,4-pentanediol, 2,2,3-trimethyl- Method H1,4-pentanediol, 2,2,4-trimethyl- 80864-10-4 1,4-pentanediol,2,3,3-trimethyl- Method H 1,4-pentanediol, 2,3,4-trimethyl- 92340-74-41,4-pentanediol, 3,3,4-trimethyl- 16466-35-6 1,5-pentanediol,2,2,3-trimethyl- Method F 1,5-pentanediol, 2,2,4-trimethyl- 3465-14-31,5-pentanediol, 2,3,3-trimethyl- Method A 1,5-pentanediol,2,3,4-trimethyl- 85373-83-7 2,4-pentanediol, 2,3,3-trimethyl- 24892-51-12,4-pentanediol, 2,3,4-trimethyl- 24892-52-2 Preferred Isomers1,3-pentanediol, 2,2,3-trimethyl- 35512-54-0 1,3-pentanediol,2,2,4-trimethyl- 144-19-4 1,3-pentanediol, 2,3,4-trimethyl- 116614-13-21,3-pentanediol, 2,4,4-trimethyl- 109387-36-2 1,3-pentanediol,3,4,4-trimethyl- 81756-50-5 1,4-pentanediol, 2,2,3-trimethyl- Method H1,4-pentanediol, 2,2,4-trimethyl- 80864-10-4 1,4-pentanediol,2,3,3-trimethyl- Method F 1,4-pentanediol, 2,3,4-trimethyl- 92340-74-41,4-pentanediol, 3,3,4-trimethyl- 16466-35-6 1,5-pentanediol,2,2,3-trimethyl- Method A 1,5-pentanediol, 2,2,4-trimethyl- 3465-14-31,5-pentanediol, 2,3,3-trimethyl- Method A 2,4-pentanediol,2,3,4-trimethyl- 24892-52-2 More Preferred Isomers 1,3-pentanediol,2,3,4-trimethyl- 116614-13-2 1,4-pentanediol, 2,3,4-trimethyl-92340-74-4 1,5-pentanediol, 2,2,3-trimethyl- Method A 1,5-pentanediol,2,2,4-trimethyl- 3465-14-3 1,5-pentanediol, 2,3,3-trimethyl- Method AETHYLMETHYLPENTANEDIOL ISOMERS Operable Isomers 1,3-pentanediol,2-ethyl-2-methyl- Method C 1,3-pentanediol, 2-ethyl-3-methyl- Method D1,3-pentanediol, 2-ethyl-4-methyl- 148904-97-6 1,3-pentanediol,3-ethyl-2-methyl- 55661-05-7 1,4-pentanediol, 2-ethyl-2-methyl- Method H1,4-pentanediol, 2-ethyl-3-methyl- Method F 1,4-pentanediol,2-ethyl-4-methyl- Method G 1,4-pentanediol, 3-ethyl-2-methyl- Method F1,4-pentanediol, 3-ethyl-3-methyl- Method F 1,5-pentanediol,2-ethyl-2-methyl- Method F 1,5-pentanediol, 2-ethyl-3-methyl- 54886-83-81,5-pentanediol, 2-ethyl-4-methyl- Method F 1,5-pentanediol,3-ethyl-3-methyl- 57740-12-2 2,4-pentanediol, 3-ethyl-2-methyl- Method GMore Preferred Isomers 1,3-pentanediol, 2-ethyl-2-methyl- Method C1,3-pentanediol, 2-ethyl-3-methyl- Method D 1,3-pentanediol,2-ethyl-4-methyl- 148904-97-6 1,3-pentanediol, 3-ethyl-2-methyl-55661-05-7 1,4-pentanediol, 2-ethyl-2-methyl- Method H 1,4-pentanediol,2-ethyl-3-methyl- Method F 1,4-pentanediol, 2-ethyl-4-methyl- Method G1,5-pentanediol, 3-ethyl-3-methyl- 57740-12-2 2,4-pentanediol,3-ethyl-2-methyl- Method G PROPYLPENTANEDIOL ISOMERS Operable Isomers1,3-pentanediol, 2-isopropyl- Method D 1,3-pentanediol, 2-propyl- MethodC 1,4-pentanediol, 2-isopropyl- Method H 1,4-pentanediol, 2-propyl-Method H 1,4-pentanediol, 3-isopropyl- Method H 1,5-pentanediol,2-isopropyl- 90951-89-6 2,4-pentanediol, 3-propyl- Method C MorePreferred Isomers 1,3-pentanediol, 2-isopropyl- Method D1,3-pentanediol, 2-propyl- Method C 1,4-pentanediol, 2-isopropyl- MethodH 1,4-pentanediol, 2-propyl- Method H 1,4-pentanediol, 3-isopropyl-Method H 2,4-pentanediol, 3-propyl- Method C DIMETHYLHEXANEDIOL ISOMERSOperable Isomers 1,3-hexanediol, 2,2-dimethyl- 22006-96-81,3-hexanediol, 2,3-dimethyl- Method D 1,3-hexanediol, 2,4-dimethyl-78122-99-3 1,3-hexanediol, 2,5-dimethyl- Method C 1,3-hexanediol,3,4-dimethyl- Method D 1,3-hexanediol, 3,5-dimethyl- Method D1,3-hexanediol, 4,4-dimethyl- Method C 1,3-hexanediol, 4,5-dimethyl-Method C 1,4-hexanediol, 2,2-dimethyl- Method F 1,4-hexanediol,2,3-dimethyl- Method F 1,4-hexanediol, 2,4-dimethyl- Method G1,4-hexanediol, 2,5-dimethyl- 22417-60-3 1,4-hexanediol, 3,3-dimethyl-Method F 1,4-hexanediol, 3,4-dimethyl- Method E 1,4-hexanediol,3,5-dimethyl- Method H 1,4-hexanediol, 4,5-dimethyl- Method E1,4-hexanediol, 5,5-dimethyl- 38624-38-3 1,5-hexanediol, 2,2-dimethyl-Method A 1,5-hexanediol, 2,3-dimethyl- 62718-05-2 1,5-hexanediol,2,4-dimethyl- 73455-82-0 1,5-hexanediol, 2,5-dimethyl- 58510-28-41,5-hexanediol, 3,3-dimethyl- 41736-99-6 1,5-hexanediol, 3,4-dimethyl-Method A 1,5-hexanediol, 3,5-dimethyl- Method G 1,5-hexanediol,4,5-dimethyl- Method F 1,6-hexanediol, 2,2-dimethyl- 13622-91-81,6-hexanediol, 2,3-dimethyl- Method F 1,6-hexanediol, 2,4-dimethyl-Method F 1,6-hexanediol, 2,5-dimethyl- 49623-11-2 1,6-hexanediol,3,3-dimethyl- Method F 1,6-hexanediol, 3,4-dimethyl- 65363-45-32,4-hexanediol, 2,3-dimethyl- 26344-17-2 2,4-hexanediol, 2,4-dimethyl-29649-22-7 2,4-hexanediol, 2,5-dimethyl- 3899-89-6 2,4-hexanediol,3,3-dimethyl- 42412-51-1 2,4-hexanediol, 3,4-dimethyl- 90951-83-02,4-hexanediol, 3,5-dimethyl- 159300-34-2 2,4-hexanediol, 4,5-dimethyl-Method D 2,4-hexanediol, 5,5-dimethyl- 108505-10-8 2,5-hexanediol,2,3-dimethyl- Method G 2,5-hexanediol, 2,4-dimethyl- Method G2,5-hexanediol, 2,5-dimethyl- 110-03-2 2,5-hexanediol, 3,3-dimethyl-Method H 2,5-hexanediol, 3,4-dimethyl- 99799-30-1 2,6-hexanediol,3,3-dimethyl- Method A More Preferred Isomers 1,3-hexanediol,2,2-dimethyl- 22006-96-8 1,3-hexanediol, 2,3-dimethyl- Method D1,3-hexanediol, 2,4-dimethyl- 78122-99-3 1,3-hexanediol, 2,5-dimethyl-Method C 1,3-hexanediol, 3,4-dimethyl- Method D 1,3-hexanediol,3,5-dimethyl- Method D 1,3-hexanediol, 4,4-dimethyl- Method C1,3-hexanediol, 4,5-dimethyl- Method C 1,4-hexanediol, 2,2-dimethyl-Method H 1,4-hexanediol, 2,3-dimethyl- Method F 1,4-hexanediol,2,4-dimethyl- Method G 1,4-hexanediol, 2,5-dimethyl- 22417-60-31,4-hexanediol, 3,3-dimethyl- Method F 1,4-hexanediol, 3,4-dimethyl-Method E 1,4-hexanediol, 3,5-dimethyl- Method H 1,4-hexanediol,4,5-dimethyl- Method E 1,4-hexanediol, 5,5-dimethyl- 38624-38-31,5-hexanediol, 2,2-dimethyl- Method A 1,5-hexanediol, 2,3-dimethyl-62718-05-2 1,5-hexanediol, 2,4-dimethyl- 73455-82-0 1,5-hexanediol,2,5-dimethyl- 58510-28-4 1,5-hexanediol, 3,3-dimethyl- 41736-99-61,5-hexanediol, 3,4-dimethyl- Method A 1,5-hexanediol, 3,5-dimethyl-Method G 1,5-hexanediol, 4,5-dimethyl- Method F 2,6-hexanediol,3,3-dimethyl- Method A ETHYLHEXANEDIOL ISOMERS More Preferred Isomers1,3-hexanediol, 2-ethyl- 94-96-2 1,3-hexanediol, 4-ethyl- Method C1,4-hexanediol, 2-ethyl- 148904-97-6 1,4-hexanediol, 4-ethyl- 1113-00-41,5-hexanediol, 2-ethyl- 58374-34-8 2,4-hexanediol, 3-ethyl- Method C2,4-hexanediol, 4-ethyl- 33683-47-5 2,5-hexanediol, 3-ethyl- Method FMETHYLHEPTANEDIOL ISOMERS Operable Isomers 1,3-heptanediol, 2-methyl-109417-38-1 1,3-heptanediol, 3-methyl- 165326-88-5 1,3-heptanediol,4-methyl- Method C 1,3-heptanediol, 5-methyl- Method D 1,3-heptanediol,6-methyl- Method C 1,4-heptanediol, 2-methyl- 15966-03-71,4-heptanediol, 3-methyl- 7748-38-1 1,4-heptanediol, 4-methyl-72473-94-0 1,4-heptanediol, 5-methyl- 63003-04-3 1,4-heptanediol,6-methyl- 99799-25-4 1,5-heptanediol, 2-methyl- 141605-00-71,5-heptanediol, 3-methyl- Method A 1,5-heptanediol, 4-methyl- Method A1,5-heptanediol, 5-methyl- 99799-26-5 1,5-heptanediol, 6-methyl-57740-00-8 1,6-heptanediol, 2-methyl- 132148-22-2 1,6-heptanediol,3-methyl- Method G 1,6-heptanediol, 4-methyl- 156307-84-51,6-heptanediol, 5-methyl- Method A 1,6-heptanediol, 6-methyl- 5392-57-42,4-heptanediol, 2-methyl- 38836-26-9 2,4-heptanediol, 3-methyl-6964-04-1 2,4-heptanediol, 4-methyl- 165326-87-4 2,4-heptanediol,5-methyl- Method C 2,4-heptanediol, 6-methyl- 79356-95-92,5-heptanediol, 2-methyl- 141605-02-9 2,5-heptanediol, 3-methyl- MethodG 2,5-heptanediol, 4-methyl- 156407-38-4 2,5-heptanediol, 5-methyl-148843-72-5 2,5-heptanediol, 6-methyl- 51916-46-2 2,6-heptanediol,2-methyl- 73304-48-0 2,6-heptanediol, 3-methyl- 29915-96-62,6-heptanediol, 4-methyl- 106257-69-6 3,4-heptanediol, 3-methyl-18938-50-6 3,5-heptanediol, 2-methyl- Method C 3,5-heptanediol,3-methyl- 99799-27-6 3,5-heptanediol, 4-methyl- 156407-37-3 MorePreferred Isomers 1,3-heptanediol, 2-methyl- 109417-38-11,3-heptanediol, 3-methyl- 165326-88-5 1,3-heptanediol, 4-methyl- MethodC 1,3-heptanediol, 5-methyl- Method D 1,3-heptanediol, 6-methyl- MethodC 1,4-heptanediol, 2-methyl- 15966-03-7 1,4-heptanediol, 3-methyl-7748-38-1 1,4-heptanediol, 4-methyl- 72473-94-0 1,4-heptanediol,5-methyl- 63003-04-3 1,4-heptanediol, 6-methyl- 99799-25-41,5-heptanediol, 2-methyl- 141605-00-7 1,5-heptanediol, 3-methyl- MethodA 1,5-heptanediol, 4-methyl- Method A 1,5-heptanediol, 5-methyl-99799-26-5 1,5-heptanediol, 6-methyl- 57740-00-8 1,6-heptanediol,2-methyl- 132148-22-2 1,6-heptanediol, 3-methyl- Method G1,6-heptanediol, 4-methyl- 156307-84-5 1,6-heptanediol, 5-methyl- MethodA 1,6-heptanediol, 6-methyl- 5392-57-4 2,4-heptanediol, 2-methyl-38836-26-9 2,4-heptanediol, 3-methyl- 6964-04-1 2,4-heptanediol,4-methyl- 165326-87-4 2,4-heptanediol, 5-methyl- Method C2,4-heptanediol, 6-methyl- 79356-95-9 2,5-heptanediol, 2-methyl-141605-02-9 2,5-heptanediol, 3-methyl- Method H 2,5-heptanediol,4-methyl- 156407-38-4 2,5-heptanediol, 5-methyl- 148843-72-52,5-heptanediol, 6-methyl- 51916-46-2 2,6-heptanediol, 2-methyl-73304-48-0 2,6-heptanediol, 3-methyl- 29915-96-6 2,6-heptanediol,4-methyl- 106257-69-6 3,4-heptanediol, 3-methyl- 18938-50-63,5-heptanediol, 2-methyl- Method C 3,5-heptanediol, 4-methyl-156407-37-3 OCTANEDIOL ISOMERS More Preferred Isomers 2,4-octanediol90162-24-6 2,5-octanediol 4527-78-0 2,6-octanediol Method A2,7-octanediol 19686-96-5 3,5-octanediol 24892-55-5 3,6-octanediol24434-09-1

TABLE V NONANEDIOL ISOMERS Chemical Name CAS No. Preferred Isomers2,4-pentanediol, 2,3,3,4-tetramethyl- 19424-43-2 Operable Isomers2,4-pentanediol, 3-tertiarybutyl- 142205-14-9 2,4-hexanediol,2,5,5-trimethyl- 97460-08-7 2,4-hexanediol, 3,3,4-trimethyl- Method D2,4-hexanediol, 3,3,5-trimethyl- 27122-58-3 2,4-hexanediol,3,5,5-trimethyl- Method D 2,4-hexanediol, 4,5,5-trimethyl- Method D2,5-hexanediol, 3,3,4-trimethyl- Method H 2,5-hexanediol,3,3,5-trimethyl- Method G

TABLE VI ALKYL GLYCERYL ETHERS, DI(HYDROXYALKYL) ETHERS, AND ARYLGLYCERYL ETHERS Preferred Monoglycerol Ethers and Derivatives1,2-propanediol,3-(butyloxy)-, triethoxylated1,2-propanediol,3-(butyloxy)-, tetraethoxylated More PreferredMonoglycerol Ethers and Derivatives CAS No.1,2-propanediol,3-(n-pentyloxy)- 22636-32-41,2-propanediol,3-(2-pentyloxy)- 1,2-propanediol,3-(3-pentyloxy)-1,2-propanediol,3-(2-methyl-1-butyloxy)-1,2-propanediol,3-(iso-amyloxy)-1,2-propanediol,3-(3-methyl-2-butyloxy)-1,2-propanediol,3-(cyclohexyloxy)-1,2-propanediol,3-(1-cyclohex-1-enyloxy)- 1,3-propanediol,2-(pentyloxy)-1,3-propanediol,2-(2-pentyloxy)- 1,3-propanediol,2-(3-pentyloxy)-1,3-propanediol,2-(2-methyl-1-butyloxy)-1,3-propanediol,2-(iso-amyloxy)-1,3-propanediol,2-(3-methyl-2-butyloxy)-1,3-propanediol,2-(cyclohexyloxy)1,3-propanediol,2-(1-cyclohex-1-enyloxy) 1,2-propanediol,3-(butyloxy)-,pentaethoxylated 1,2-propanediol,3-(butyloxy)-, hexaethoxylated1,2-propanediol,3-(butyloxy)-, heptaethoxylated1,2-propanediol,3-(butyloxy)-, octaethoxylated1,2-propanediol,3-(butyloxy)-, nonaethoxylated1,2-propanediol,3-(butyloxy)-, monopropoxylated1,2-propanediol,3-(butyloxy)-, dibutyleneoxylated1,2-propanediol,3-(butyloxy)-, tributyleneoxylated More PreferredDi(hydroxvalkyl) Ethers bis(2-hydroxybutyl) etherbis(2-hydroxycyclopentyl) ether AROMATIC GLYCERYL ETHERS OperableAromatic Glyceryl Ethers 1,2-propanediol,3-phenyloxy-1,2-propanediol,3-benzyloxy- 1,2-propanediol,3-(2-phenylethyloxy)1,2-propanediol,3-(1-phenyl-2-propanyloxy)- 1,3-propanediol,2-phenyloxy-1,3-propanediol,2-(m-cresyloxy)- 1,3-propanediol,2-(p-cresyloxy)-1,3-propanediol,2-benzyloxy- 1,3-propanediol,2-(2-phenylethyloxy)-1,3-propanediol,2-(1-phenylethyloxy)- Preferred Aromatic Glyceryl Ethers1,2-propanediol,3-phenyloxy- 1,2-propanediol,3-benzyloxy-1,2-propanediol,3-(2-phenylethyloxy)- 1,3-propanediol,2-(m-cresyloxy)-1,3-propanediol,2-(p-cresyloxy)- 1,3-propanediol,2-benzyloxy-1,3-propanediol,2-(2-phenylethyloxy)- Preferred Aromatic Glyceryl Ethers1,2-propanediol,3-phenyloxy- 1,2-propanediol,3-benzyloxy-1,2-propanediol,3-(2-phenylethyloxy)- 1,3-propanediol,2-(m-cresyloxy)1,3-propanediol,2-(p-cresyloxy)- 1,3-propanediol,2-(2-phenylethyloxy)

TABLE VII ALICYCLIC DiOLS AND DERIVATIVES Chemical Name CAS No.Preferred Cylic Diols and Derivatives 1-isopropyl-1,2-cyclobutanediol59895-32-8 3-ethyl-4-methyl-1,2-cyclobutanediol3-propyl-1,2-cyclobutanediol 3-isopropyl-1,2-cyclobutanediol 42113-90-61-ethyl-1,2-cyclopentanediol 67396-17-21,2-dimethyl-1,2-cyclopentanediol 33046-20-71,4-dimethyl-1,2-cyclopentanediol 89794-56-92,4,5-trimethyl-1,3-cyclopentanediol 3,3-dimethyl-1,2-cyclopentanediol89794-57-0 3,4-dimethyl-1,2-cyclopentanediol 70051-69-33,5-dimethyl-1,2-cyclopentanediol 89794-58-13-ethyl-1,2-cyclopentanediol 4,4-dimethyl-1,2-cyclopentanediol70197-54-5 4-ethyl-1,2-cyclopentanediol1,1-bis(hydroxymethyl)cyclohexane 2658-60-81,2-bis(hydroxymethyl)cyclohexane 76155-27-61,2-dimethyl-1,3-cyclohexanediol 53023-07-71,3-bis(hydroxymethyl)cyclohexane 13022-98-51,3-dimethyl-1,3-cyclohexanediol 128749-93-91,6-dimethyl-1,3-cyclohexanediol 164713-16-01-hydroxy-cyclohexaneethanol 40894-17-5 1-hydroxy-cyclohexanemethanol15753-47-6 1-ethyl-1,3-cyclohexanediol 10601-18-01-methyl-1,2-cyclohexanediol 52718-65-7 2,2-dimethyl-1,3-cyclohexanediol114693-83-3 2,3-dimethyl-1,4-cyclohexanediol 70156-82-02,4-dimethyl-1,3-cyclohexanediol 2,5-dimethyl-1,3-cyclohexanediol2,6-dimethyl-1,4-cyclohexanediol 34958-42-4 2-ethyl-1,3-cyclohexanediol155433-88-8 2-hydroxycyclohexaneethanol 24682-42-62-hydroxyethyl-1-cyclohexanol 2-hydroxymethylcyclohexanol 89794-52-53-hydroxyethyl-1-cyclohexanol 3-hydroxycyclohexaneethanol 86576-87-63-hydroxymethylcyclohexanol 3-methyl-1,2-cyclohexanediol 23477-91-04,4-dimethyl-1,3-cyclohexanediol 14203-50-04,5-dimethyl-1,3-cyclohexanediol 4,6-dimethyl-1,3-cyclohexanediol16066-66-3 4-ethyl-1,3-cyclohexanediol 4-hydroxyethyl-1-cyclohexanol4-hydroxymethylcyclohexanol 33893-85-5 4-methyl-1,2-cyclohexanediol23832-27-1 5,5-dimethyl-1,3-cyclohexanediol 51335-83-25-ethyl-1,3-cyclohexanediol 1,2-cycloheptanediol 108268-28-62-methyl-1,3-cycloheptanediol 101375-80-8 2-methyl-1,4-cycloheptanediol4-methyl-1,3-cycloheptanediol 5-methyl-1,3-cycloheptanediol5-methyl-1,4-cycloheptanediol 90201-00-6 6-methyl-1,4-cycloheptanediol1,3-cyclooctanediol 101935-36-8 1,4-cyclooctanediol 73982-04-41,5-cyclooctanediol 23418-82-8 1,2-cyclohexanediol, diethoxylate1,2-cyclohexanediol, triethoxylate 1,2-cyclohexanediol, tetraethoxylate1,2-cyclohexanediol, pentaethoxylate 1,2-cyclohexanediol, hexaethoxylate1,2-cyclohexanediol, heptaethoxylate 1,2-cyclohexanediol, octaethoxylate1,2-cyclohexanediol, nonaethoxylate 1,2-cyclohexanediol, monopropoxylate1,2-cyclohexanediol, monobutylenoxylate 1,2-cyclohexanediol,dibutylenoxylate 1,2-cyclohexanediol, tributylenoxylate More PreferredCylic Diols and Derivatives 1-isopropyl-1,2-cyclobutanediol 59895-32-83-ethyl-4-methyl-1,2-cyclobutanediol 3-propyl-1,2-cyclobutanediol3-isopropyl-1,2-cyclobutanediol 42113-90-6 1-ethyl-1,2-cyclopentanediol67396-17-2 1,2-dimethyl-1,2-cyclopentanediol 33046-20-71,4-dimethyl-1,2-cyclopentanediol 89794-56-93,3-dimethyl-1,2-cyclopentanediol 89794-57-03,4-dimethyl-1,2-cyclopentanediol 70051-69-33,5-dimethyl-1,2-cyclopentanediol 89794-58-13-ethyl-1,2-cyclopeutanediol 4,4-dimethyl-1,2-cyclopentanediol70197-54-5 4-ethyl-1,2-cyclopentanediol1,1-bis(hydroxymethyl)cyclohexane 2658-60-81,2-bis(hydroxymethyl)cyclohexane 76155-27-61,2-dimethyl-1,3-cyclohexanediol 53023-07-71,3-bis(hydroxymethyl)cyclohexane 13022-98-51-hydroxy-cyclohexanemethanol 15753-47-6 1-methyl-1,2-cyclohexanediol52718-65-7 3-hydroxymethylcyclohexanol 3-methyl-1,2-cyclohexanediol23477-91-0 4,4-dimethyl-1,3-cyclohexanediol 14203-50-04,5-dimethyl-1,3-cyclohexanediol 4,6-dimethyl-1,3-cyclohexanediol16066-66-3 4-ethyl-1,3-cyclohexanediol 4-hydroxyethyl-1-cyclohexanol4-hydroxymethylcyclohexanol 33893-85-5 4-methyl-1,2-cyclohexanediol23832-27-1 1,2-cycloheptanediol 108268-28-6 1,2-cyclohexanediol,pentaethoxylate 1,2-cyclohexanediol, hexaethoxylate 1,2-cyclohexanediol,heptaethoxylate 1,2-cyclohexanediol, octaethoxylate 1,2-cyclohexanediol,nonaethoxylate 1,2-cyclohexanediol, monopropoxylate 1,2-cyclohexanediol,dibutylenoxylate

The unsaturated alicyclic diols include the following known unsaturatedalicyclic diols:

Operable Unsaturated Alicyclic Diols Chemical Name CAS No.1,2-Cyclobutanediol,1-ethenyl-2-ethyl- 58016-14-13-Cyclobutene-1,2-diol,1,2,3,4-tetramethyl- 90112-64-43-Cyclobutene-1,2-diol,3,4-diethyl- 142543-60-03-Cyclobutene-1,2-diol,3-(1,1-dimethylethyl)- 142543-56-43-Cyclobutene-1,2-diol,3-butyl- 142543-55-31,2-Cyclopentanediol,1,2-dimethyl-4-methylene- 103150-02-31,2-Cyclopentanediol,1-ethyl-3-methylene- 90314-52-61,2-Cyclopentanediol,4-(1-propenyl) 128173-45-53-Cyclopentene-1,2-diol,1-ethyl-3-methyl- 90314-43-51,2-Cyclohexanediol,1-ethenyl- 134134-16-01,2-Cyclohexanediol,1-methyl-3-methylene- 98204-78-51,2-Cyclohexanediol,1-methyl-4-methylene- 133358-53-91,2-Cyclohexanediol,3-ethenyl- 55310-51-5 1,2-Cyclohexanediol,4-ethenyl-85905-16-4 3-Cyclohexene-1,2-diol,2,6-dimethyl- 81969-75-73-Cyclohexene-1,2-diol,6,6-dimethyl- 61875-93-24-Cyclohexene-1,2-diol,3,6-dimethyl- 156808-73-04-Cyclohexene-1,2-diol,4,5-dimethyl- 154351-54-9 3-Cyclooctene-1,2-diol170211-27-5 4-Cyclooctene-1,2-diol 124791-61-3 5-Cyclooctene-1,2-diol117468-07-2

TABLE VIII C₃C₇DIOL ALKOXYLATED DERIVATIVES

In the following tables, “EO” means polyethoxylates, i.e.,—(CH₂CH₂O)_(n)H; Me-E_(n) means methyl-capped polyethoxylates—(CH₂CH₂O)_(n)CH₃; “2(Me-En)” means 2 Me-En groups needed; “PO” meanspolypropoxylates, —(CH(CH₃)CH₂O)_(n)H; “BO” means polybutyleneoxygroups, (CH(CH₂CH₃)CH₂O)_(n)H; and “n-BO” means poly(n-butyleneoxy) orpoly(tetramethylene)oxy groups —(CH₂CH₂CH₂CH₂O)_(n)H. The indicatedalkoxylated derivatives are all operable and those that are preferredare in bold type and listed on the second line. Non-limiting, typicalsynthesis methods to prepare the alkoxylated derivatives are given inthe copending application Ser. No. 08/679,694, filed Jul. 11, 1996incorporated hereinbefore by reference.

TABLE VIIIA Base Material EO's 1(Me—En) 2(Me—En) PO's n-BO's BO's BaseMaterial^((a)) CAS No. (b) (c) (d) (e) (f) (g) 1,2-propanediol (C3)57-55-6 1-4 3-4 4 1,2-propanediol, 55843-0  4-10 1 2-methyl-(C4)  8-10 13 1,3-propanediol (C3) 504-63-2 6-8 5-6 8 6 1,3-propanediol, 115-76-41-7 1-2 2,2-diethyl-(C7) 4-7 1 2 1,3-propanediol, 126-30-7 3-42,2-dimethyl-(C5) 1-2 4 1,3-propanediol,2-(1- 33673-01-7 1-7 1-2methylpropyl)-(C7) 4-7 1 2 1,3-propanediol,2-(2- 26462-20-8 1-7 1-2methylpropyl)-(C7) 4-7 1 2 1,3-propanediol, 2612-29-5  6-10 2-ethyl-(C5) 9-10 1 3 1,3-propanediol,2- 77-84-9 1-6 ethyl-2-methyl-(C6) 3-6 2 11,3-propanediol, 2612-27-3 1-6 2-isopropyl-(C6) 3-6 2 1 1,3-propanediol,216342-0 2-5 4-5 2-methyl-(C4) 4-5 5 2 1,3-propanediol,2- 2109-23-1 2-91-3 methyl-2-isopropyl- 6-9 1 2-3 (C7) 1,3-propanediol,2- 78-26-2 1-71-2 methyl-2-propyl-(C7) 4-7 1 2 1,3-propanediol, 2612-284 12-propyl-(C6) 1-4 2 (a) The number of indicated alkoxylated groups inthis and following Tables VIII are all operable, the generic limitsbeing listed on the first line, and those that are preferred are in boldtype and listed on the second line. (b) The numbers in this column areaverage numbers of (CH₂CH₂O) groups in the polyethoxylated derivative.(c) The numbers in this column are average numbers of (CH₂CH₂O) groupsin the one methyl-capped polyethoxylate substituant in each derivative.(d) The numbers in this column &e average numbers of (CH₂CH₂O) groups ineach of the two methyl-capped polyethoxylate substituants in eachderivative. (e) The numbers in this column are average numbers of(CH(CH₃)CH₂O) groups in the polypropoxylated derivative. (f) The numbersin this column are average numbers of (CH₂CH₂CH₂CH₂O) groups in thepolytetratmethyleneoxylated derivative. (g) The numbers in this columnare average numbers of (CH(CH₂CH₃)CH₂O) groups in the polybutoxylatedderivative.

TABLE VIIIB Base Material EO's 1(Me—En) 2(Me—En) PO's n-BO's BO's BaseMaterial^((a)) CAS No. (b) (c) (d) (e) (f) (g) 1,2-butanediol (C4)584-03-2 2-8 6-8 2-3 1 1,2-butanediol, 66553-15-9 1-6 1-2 2,3-dimethyl-(C6) 2-5 1 1,2-butanediol, 66553-16-0 2-ethyl- (C6) 1-3 11,2-butanediol, 41051-72-3 2-methyl- (C5) 1-2 1 1,2-butanediol,59562-82-2 1-6 1-2 3,3-dimethyl- (C6) 2-5 1 1,2-butanediol, 50468-22-93-methyl- (C5) 1-2 1 1,3-butanediol (C4) 107-88-0 3-6 5 5-6 21,3-butanediol,2, 16343-75-2 1-2 2,3-trimethyl- (C7) 1-3 21,3-butanediol,2, 76-35-7 3-8 2-dimethyl- (C6) 6-8 3 1,3-butanediol,24893-35-4 3-8 2,3-dimethyl- (C6) 6-8 3 1,3-butanediol, 66553-17-1 1-62-ethyl- (C6) 4-6 2 to 3 1 1,3-butanediol,2- Method C 2-4ethyl-2-methyl- (C7) 1 1 3 1,3-butanediol,2- 68799-03-1 2-4ethyl-3-methyl- (C7) 1 1 3 1,3-butanediol, 66567-04-2 2-4 2-isopropyl-(C7) 1 1 3 1,3-butanediol, 684-84-4 1-3 2-methyl- (C5) 2-3 41,3-butanediol, 66567-03-1 2-9 1-3 2-propyl- (C7) 6-8 1 2-31,3-butanediol, 2568-33-4 1-3 3-methyl- (C5) 2-3 4 1,4-butanediol (C4)110-63-4 2-4 4-5 2 3-4 4-5 1,4-butanediol,2, 162108-60-3 2-9 1-32,3-trimethyl- (C7) 6-9 1 2-3 1,4-butanediol, 32812-23-0 1-62,2-dimethyl- (C6) 3-6 2 1 1,4-butanediol, 57716-80-0 1-6 2,3-dimethyl-(C6) 3-6 2 1 1,4-butanediol, 57716-79-7 1 2-ethyl- (C6) 1-4 21,4-butanediol,2- 76651-98-4 1-7 1-2 ethyl-2-methyl- (C7) 4-7 1 21,4-butanediol,2- 66225-34-1 1-7 1-2 ethyl-3-methyl- (C7) 4-7 1 21,4-butanediol, 39497-66-0 1-7 1-2 2-isopropyl- (C7) 4-7 1 21,4-butanediol, 2938-98-9  6-10 1 2-methyl- (C5)  9-10 1 31,4-butanediol, 62946-68-3 1-5 1-2 2-propyl- (C7) 2-5 11,4-butanediol,3- Method F 2-9 1-3 ethyl-1-methyl- (C7) 6-8 1 2-32,3-butanediol (C4) 513-85-9  6-10 1  9-10 1 3-4 2,3-butanediol, 76-09-53-9 1-3 2,3-dimethyl- (C6) 7-9 1 2-3 2,3-butanediol, 5396-58-7 1-52-methyl- (C5) 2-5 2 1 (a) The number of indicated alkoxylated groups inthis Table are all operable, the generic limits being listed on thefirst line, and those that are preferred are in bold type and listed onthe second line. (b) The numbers in this column are average numbers of(CH₂CH₂O) groups in the polyethoxylated derivative. (c) The numbers inthis column are average numbers of (CH₂CH₂O) groups in the onemethyl-capped polyethoxylate substituant in each derivative. (d) Thenumbers in this column are average numbers of (CH₂CH₂O) groups in eachof the two methyl-capped polyethoxylate substituants in each derivative.(e) The numbers in this column are average numbers of (CH(CH₃)CH₂O)groups in the polypropoxylated derivative. (f) The numbers in thiscolumn are average numbers of (CH₂CH₂CH₂CH₂O) groups in thepolytetramethyleneoxylated derivative. (g) The numbers in this columnare average numbers of (CH(CH₂CH₃)CH₂O) groups in the polybutoxylatedderivative.

TABLE VIIIC Base Material EO's 1(Me—En) 2(Me—En) PO's n-BO's BO's BaseMaterial^((a)) CAS No. (b) (c) (d) (e) (f) (g) 1,2-pentanediol 5343-92-0 3-10 2-3 (C5)  7-10 1 3 1,2-pentanediol, 20667-05-4 2-methyl- (C6) 1-31 1,2-pentanediol, 159623-53-7 3-methyl- (C6) 1-3 1 1,2-pentanediol,72110-08-8 4-methyl- (C6) 1-3 1 1,3-pentanediol 3174-67-2 (C5) 1-2 3-41,3-pentanediol, 2157-31-5 2-4 2,2-dimethyl- (C7) 1 1 3 1,3-pentanediol,66225-52-3 2-4 2,3-dimethyl- (C7) 1 1 3 1,3-pentanediol, 60712-38-1 2-42,4-dimethyl- (C7) 1 1 3 1,3-pentanediol, 29887-11-4 2-9 1-3 2-ethyl-(C7) 6-8 1 2-3 1,3-pentanediol, 149-31-5 1-6 1 2-methyl- (C6) 4-6 2-31,3-pentanediol, 129851-50-9 2-4 3,4-dimethyl- (C7) 1 1 31,3-pentanediol, 33879-72-0 1-6 1 3-methyl- (C6) 4-6 2-31,3-pentanediol, 30458-16-3 2-4 4,4-dimethyl- (C7) 1 1 31,3-pentanediol, 54876-99-2 1-6 1 4-methyl- (C6) 4-6 2-3 1,4-pentanediol626-95-9 (C5) 1-2 3-4 1,4-pentanediol, Method F 2-4 2,2-dimethyl- (C7) 11 3 1,4-pentanediol, Method F 2-4 2,3-dimethyl- (C7) 1 1 31,4-pentanediol, Method F 2-4 2,4-dimethyl- (C7) 1 1 3 1,4-pentanediol,6287-17-8 1-6 1 2-methyl- (C6) 4-6 2-3 1,4-pentanediol, 81887-62-9 2-43,3-dimethyl- (C7) 1 1 3 1,4-pentanediol, 63521-36-8 2-4 3,4-dimethyl-(C7) 1 1 3 1,4-pentanediol, 26787-63-3 1-6 1 3-methyl- (C6) 4-6 2-31,4-pentanediol, 1462-10-8 1-6 1 4-methyl- (C6) 4-6 2-3 1,5-pentanediol111-29-5  4-10 (C5)  8-10 1 3 1,5-pentanediol, 3121-82-2 1-7 1-22,2-dimethyl- (C7) 4-7 1 2 1,5-pentanediol, 81554-20-3 1-7 1-22,3-dimethyl- (C7) 4-7 1 2 1,5-pentanediol, 2121-69-9 1-7 1-22,4-dimethyl- (C7) 4-7 1 2 1,5-pentanediol, 14189-13-0 1-5 1-2 2-ethyl-(C7) 2-5 1 1,5-pentanediol, 42856-62-2 2-methyl- (C6) 1-4 21,5-pentanediol, 53120-74-4 1-7 1-2 3,3-dimethyl- (C7) 4-7 1 21,5-pentanediol, 4457-71-0 3-methyl- (C6) 1-4 2 2,3-pentanediol42027-23-6 (C5) 1-3 2 2,3-pentanediol, 7795-80-4 1-7 1-2 2-methyl- (C6)4-7 1 2 2,3-pentanediol, 63521-37-9 1-7 1-2 3-methyl- (C6) 4-7 1 22,3-pentanediol, 7795-79-1 1-7 1-2 4-methyl- (C6) 4-7 1 22,4-pentanediol 625-69-4 1-4 (C5) 2-4 4 2,4-pentanediol, 24893-39-8 1-42,3-dimethyl- (C7) 2-4 2 2,4-pentanediol, 24892-49-7 1-4 2,4-dimethyl-(C7) 2-4 2 2,4-pentanediol, 107-41-5  5-10 2-methyl- (C6)  8-102,4-pentanediol, 24892-50-0 1-4 3,3-dimethyl- (C7) 2-4 22,4-pentanediol, Method H  5-10 3-methyl- (C6)  8-10 3 (a) The number ofindicated alkoxylated groups in this Table are all operable, the genericlimits being listed on the first line, and those that are preferred arein bold type and listed on the second line. (b) The numbers in thiscolumn are average numbers of (CH₂CH₂O) groups in the polyethoxylatedderivative. (c) The numbers in this column are average numbers of(CH₂CH₂O) groups in the one methyl-capped polyethoxylate substituant ineach derivative. (d) The numbers in this column are average numbers of(CH₂CH₂O) groups in each of the two methyl-capped polyethoxylatesubstituants in each derivative. (e) The numbers in this column areaverage numbers of (CH(CH₃)CH₂O) groups in the polypropoxylatedderivative. (f) The numbers in this column are average numbers of(CH₂CH₂CH₂CH₂O) groups in th& polytetramethyleneoxylated derivative. (g)The numbers in this column are average numbers of (CH(CH₂CH₃)CH₂O)groups in the polybutoxylated derivative.

TABLE VIIID Base Material EO's 1(Me—En) PO's n-BO's BO's BaseMaterial^((a)) CAS No. (b) (c) (e) (f) (g) 1,3-hexanediol (C6)21531-91-9 1-5 2-5 2 1 1,3-hexanediol, 66072-21-7 2-9 1-3 1 2-methyl-(C7) 6-8 1 2-3 1,3-hexanediol, Method D 2-9 1-3 3-methyl- (C7) 6-8 1 2-31,3-hexanediol, Method C 2-9 1-3 4-methyl- (C7) 6-8 1 2-31,3-hexanediol, 109863-14-1 2-9 1-3 5-methyl- (C7) 6-8 1 2-31,4-hexanediol (C6) 16432-53-4 1-5 2-5 2 1 1,4-hexanediol, Method F 2-91-3 2-methyl- (C7) 6-8 1 2-3 1,4-hexanediol, 66225-36-3 2-9 1-33-methyl- (C7) 6-8 1 2-3 1,4-hexanediol, 40646-08-0 2-9 1-3 4-methyl-(C7) 6-8 1 2-3 1,4-hexanediol, 38624-36-1 2-9 1-3 5-methyl- (C7) 6-8 12-3 1,5-hexanediol (C6) 928-40-5 1-5 2-5 2 1 1,5-hexanediol, Method F2-9 1-3 2-methyl- (C7) 6-8 1 2-3 1,5-hexanediol, Method F 2-9 1-33-methyl- (C7) 6-8 1 2-3 1,5-hexanediol, 66225-37-4 2-9 1-3 4-methyl-(C7) 6-8 1 2-3 1,5-hexanediol, 1462-11-9 2-9 1-3 5-methyl- (C7) 6-8 12-3 1,6-hexanediol (C6) 629-11-8 1-2 1-2 4 1,6-hexanediol, 25258-92-81-5 1-2 2-methyl- (C7) 2-5 1 1,6-hexanediol, 4089-71-8 1-5 1-2 3-methyl-(C7) 2-5 1 2,3-hexanediol (C6) 617-30-1 1-5 1-2 2-5 1 2,4-hexanediol(C6) 19780-90-6 3-8 5-8 3 2,4-hexanediol, 66225-35-2 2-methyl- (C7) 1-21-2 2,4-hexanediol, 16530-79-1 3-methyl- (C7) 1-2 1-2 2,4-hexanediol,38836-25-8 4-methyl- (C7) 1-2 1-2 2,4-hexanediol, 54877-00-8 5-methyl-(C7) 1-2 1-2 2,5-hexanediol (C6) 2935-44-6 3-8 5-8 3 2,5-hexanediol,29044-06-2 2-methyl- (C7) 1-2 1-2 2,5-hexanediol, Method H 3-methyl-(C7) 1-2 1-2 3,4-hexanediol (C6) 922-17-8 1-5 2-5 1 (a) The number ofindicated alkoxylated groups in this Table are all operable, the genericlimits being listed on the first line, and those that are preferred arein bold type and listed on the second line. (b) The numbers in thiscolumn are average numbers of (CH₂CH₂O) groups in the polyethoxylatedderivative. (c) The numbers in this column are average numbers of(CH₂CH₂O) groups in the one methyl-capped polyethoxylate substituant ineach derivative. (e) The numbers in this column are average numbers of(CH(CH₃)CH₂O) groups in the polypropoxylated derivative. (f) The numbersin this column are average numbers of (CH₂CH₂CH₂CH₂O) groups in thepolytetramethyleneoxylated derivative. (g) The numbers in this columnare average numbers of (CH(CH₂CH₃)CH₂O) groups in the polybutoxylatedderivative.

TABLE VIIIE Base Material EO's 1(Me—En) PO's n-BO's Base Material^((a))CAS No. (b) (c) (e) (f) 1,3-heptanediol (C7) 23433-04-7 1-7 1-2 3-6 1 21,4-heptanediol (C7) 40646-07-9 1-7 1-2 3-6 1 2 1,5-heptanediol (C7)60096-09-5 1-7 1-2 3-6 1 2 1,6-heptanediol (C7) 13175-27-4 1-7 1-2 3-6 12 1,7-heptanediol (C7) 629-30-1 1-2 1 2,4-heptanediol (C7) 20748-86-1 3-10  7-10 1 1 3 2,5-heptanediol (C7) 70444-25-6  3-10  7-10 1 1 32,6-heptanediol (C7) 5969-12-0  3-10  7-10 1 1 3 3,5-heptanediol (C7)86632-40-8  3-10  7-10 1 1 3 ^((a))The number of indicated alkoxylatedgroups in this Table are all operable, the generic limits being listedon the first line, and those that are preferred are in bold type andlisted on the second line. (b) The numbers in this column are averagenumbers of (CH₂CH₂O) groups in the polyethoxylated derivative. (c) Thenumbers in this column are average numbers of (CH₂CH₂O) groups in theone methyl-capped polyethoxylate substituant in each derivative. (e) Thenumbers in this column are average numbers of (CH(CH₃)CH₂O) groups thepolypropoxylated derivative. (f) The numbers in this column are averagenumbers of (CH₂CH₂CH₂CH₂O) groups in the polytetramethyleneoxylatedderivative.

TABLE IX AROMATIC DIOLS Suitable aromatic diols include: Chemical NameCAS No. Operable Aromatic Diols 1-phenyl-1,2-ethanediol 93-56-11-phenyl-1,2-propanediol 1855-09-0 2-phenyl-1,2-propanediol 87760-50-73-phenyl-1,2-propanediol 17131-14-5 1-(3-methylphenyl)-1,3-propanediol5169943-5 1-(4-methylphenyl)-1,3-propanediol 159266-06-52-methyl-1-phenyl-1,3-propanediol 139068-60-3 1-phenyl-1,3-butanediol118100-60-0 3-phenyl-1,3-butanediol 68330-54-1 1-phenyl-1,4-butanediol136173-88-1 2-phenyl-1,4-butanediol 95840-73-6 1-phenyl-2,3-butanediol169437-68-7 Preferred Aromatic Diols 1-phenyl-1,2-ethanediol 93-56-11-phenyl-1,2-propanediol 1855-09-0 2-phenyl-1,2-propanediol 87760-50-73-phenyl-1,2-propanediol 17131-14-5 1-(3-methylphenyl)-1,3-propanediol51699-43-5 1-(4-methylphenyl)-1,3-propanediol 159266-06-52-methyl-1-phenyl-1,3-propanediol 139068-60-3 1-phenyl-1,3-butanediol118100-60-0 3-phenyl-1,3-butanediol 68330-54-1 1-phenyl-1,4-butanediol136173-88-1 More Preferred Aromatic Diols 1-phenyl-1,2-propanediol1855-09-0 2-phenyl-1,2-propanediol 87760-50-7 3-phenyl-1,2-propanediol17131-14-5 1-(3-methylphenyl)-1,3-propanediol 51699-43-51-(4-methylphenyl)-1,3-propanediol 159266-06-52-methyl-1-phenyl-1,3-propanediol 139068-60-3 3-phenyl-1,3-butanediol68330-54-1 1-phenyl-1,4-butanediol 136173-88-1

X. principal solvents which are homologs, or analogs, of the abovestructures where the total number of hydrogen atoms is increased by theaddition of one, or more additional CH₂ groups, the total number ofhydrogen atoms being kept at the same number by introducing doublebonds, are also useful with examples including the following knowncompounds:

TABLE X EXAMPLES OF UNSATURATED COMPOUNDS Operable Unsaturated Diols1,3-Propanediol,2,2-di-2-propenyl- 55038-13-61,3-Propanediol,2-(1-pentenyl)- 138436-18-71,3-Propanediol,2-(2-methyl-2-propenyl)-2-(2-propenyl)- 121887-76-11,3-Propanediol,2-(3-methyl-1-butenyl)- 138436-17-61,3-Propanediol,2-(4-pentenyl)- 73012-46-11,3-Propanediol,2-ethyl-2-(2-methyl-2-propenyl)- 91367-61-21,3-Propanediol,2-ethyl-2-(2-propenyl)- 27606-26-41,3-Propanediol,2-methyl-2-(3-methyl-3-butenyl)- 132130-95-11,3-Butanediol,2,2-diallyl- 103985-49-51,3-Butanediol,2-(1-ethyl-1-propenyl)- 116103-35-61,3-Butanediol,2-(2-butenyl)-2-methyl- 92207-83-51,3-Butanediol,2-(3-methyl-2-butenyl)- 98955-19-21,3-Butanediol,2-ethyl-2-(2-propenyl)- 122761-93-71,3-Butanediol,2-methyl-2-(1-methyl-2-propenyl)- 141585-58-21,4-Butanediol,2,3-bis(1-methylethylidene)- 52127-63-61,4-Butanediol,2-(3-methyl-2-butenyl)-3-methylene- 115895-78-82-Butene-1,4-diol,2-(1,1-dimethylpropyl)- 91154-01-72-Butene-1,4-diol,2-(1-methylpropyl)- 91154-00-62-Butene-1,4-diol,2-butyl- 153943-66-91,3-Pentanediol,2-ethenyl-3-ethyl- 104683-37-61,3-Pentanediol,2-ethenyl-4,4-dimethyl- 143447-08-91,4-Pentanediol,3-methyl-2-(2-propenyl)- 139301-86-31,5-Pentanediol,2-(1-propenyl)- 84143-44-21,5-Pentanediol,2-(2-propenyl)- 134757-01-01,5-Pentanediol,2-ethylidene-3-methyl- 42178-93-81,5-Pentanediol,2-propylidene- 58203-50-22,4-Pentanediol,3-ethylidene-2,4-dimethyl- 88610-19-94-Pentene-1,3-diol,2-(1,1-dimethylethyl)- 109788-04-74-Pentene-1,3-diol,2-ethyl-2,3-dimethyl- 90676-97-41,4-Hexanediol,4-ethyl-2-methylene- 66950-87-61,5-Hexadiene-3,4-diol,2,3,5-trimethyl- 18984-03-71,5-Hexadiene-3,4-diol,5-ethyl-3-methyl- 18927-12-31,5-Hexanediol,2-(1-methylethenyl)- 96802-18-5 1,6-Hexanediol,2-ethenyl-66747-31-7 1-Hexene-3,4-diol,5,5-dimethyl- 169736-29-21-Hexene-3,4-diol,5,5-dimethyl- 120191-04-02-Hexene-1,5-diol,4-ethenyl-2,5-dimethyl- 70101-76-73-Hexene-1,6-diol,2-ethenyl-2,5-dimethyl- 112763-52-73-Hexene-1,6-diol,2-ethyl- 84143-45-3 3-Hexene-1,6-diol,3,4-dimethyl-125032-66-8 4-Hexene-2,3-diol,2,5-dimethyl- 13295-61-94-Hexene-2,3-diol,3,4-dimethyl- 135367-17-85-Hexene-1,3-diol,3-(2-propenyl)- 74693-24-65-Hexene-2,3-diol,2,3-dimethyl- 154386-00-25-Hexene-2,3-diol,3,4-dimethyl- 135096-13-85-Hexene-2,3-diol,3,5-dimethyl- 134626-63-45-Hexene-2,4-diol,3-ethenyl-2,5-dimethyl- 155751-24-91,4-Heptanediol,6-methyl-5-methylene- 100590-29-21,5-Heptadiene-3,4-diol,2,3-dimethyl- 18927-06-51,5-Heptadiene-3,4-diol,2,5-dimethyl- 22607-16-51,5-Heptadiene-3,4-diol,3,5-dimethyl- 18938-51-71,7-Heptanediol,2,6-bis(methylene)- 139618-24-91,7-Heptanediol,4-methylene- 71370-08-6 1-Heptene-3,5-diol,2,4-dimethyl-155932-77-7 1-Heptene-3,5-diol,2,6-dimethyl- 132157-35-81-Heptene-3,5-diol,3-ethenyl-5-methyl 61841-10-91-Heptene-3,5-diol,6,6-dimethyl- 109788-01-42,4-Heptadiene-2,6-diol,4,6-dimethyl- 102605-95-82,5-Heptadiene-1,7-diol,4,4-dimethyl- 162816-19-52,6-Heptadiene-1,4-diol,2,5,5-trimethyl- 115346-30-02-Heptene-1,4-diol,5,6-dimethyl- 103867-76-1 2-Heptene-1,5-diol,5-ethyl-104683-39-8 2-Heptene-1,7-diol,2-methyl- 74868-68-13-Heptene-1,5-diol,4,6-dimethyl- 14702845-33-Heptene-1,7-diol,3-methyl-6-methylene- 109750-55-23-Heptene-2,5-diol,2,4-dimethyl- 98955-40-93-Heptene-2,5-diol,2,5-dimethyl- 24459-23-23-Heptene-2,6-diol,2,6-dimethyl- 160524-66-33-Heptene-2,6-diol,4,6-dimethyl- 59502-66-85-Heptene-1,3-diol,2,4-dimethyl- 123363-69-9 5-Heptene-1,3 -diol,3,6-dimethyl- 96924-52-6 5-Heptene-1,4-diol,2,6-dimethyl- 106777-98-45-Heptene-1,4-diol,3,6-dimethyl- 106777-99-55-Heptene-2,4-diol,2,3-dimethyl- 104651-56-16-Heptene-1,3-diol,2,2-dimethyl- 140192-39-86-Heptene-1,4-diol,4-(2-propenyl)- 1727-87-36-Heptene-1,4-diol,5,6-dimethyl- 152344-16-66-Heptene-1,5-diol,2,4-dimethyl- 74231-27-96-Heptene-1,5-diol,2-ethylidene-6-methyl- 91139-73-06-Heptene-2,4-diol,4-(2-propenyl)- 101536-75-86-Heptene-2,4-diol,5,5-dimethyl- 98753-77-66-Heptene-2,5-diol,4,6-dimethyl- 134876-94-16-Heptene-2,5-diol,5-ethenyl-4-methyl- 65757-31-51,3-Octanediol,2-methylene- 108086-78-81,6-Octadiene-3,5-diol,2,6-dimethyl- 91140-06-61,6-Octadiene-3,5-diol,3,7-dimethyl- 75654-19-21,7-Octadiene-3,6-diol,2,6-dimethyl- 51276-33-61,7-Octadiene-3,6-diol,2,7-dimethyl- 26947-10-41,7-Octadiene-3,6-diol,3,6-dimethyl- 31354-73-11-Octene-3,6-diol,3-ethenyl- 65757-34-82,4,6-Octatriene-1,8-diol,2,7-dimethyl- 162648-63-72,4-Octadiene-1,7-diol,3,7-dimethyl- 136054-24-52,5-Octadiene-1,7-diol,2,6-dimethyl- 91140-07-72,5-Octadiene-1,7-diol,3,7-dimethyl- 117935-59-82,6-Octadiene-1,4-diol,3,7-dimethyl- (Rosiridol) 101391-01-92,6-Octadiene-1,8-diol,2-methyl- 149112-02-72,7-Octadiene-1,4-diol,3,7-dimethyl- 91140-08-82,7-Octadiene-1,5-diol,2,6-dimethyl- 91140-09-92,7-Octadiene-1,6-diol,2,6-dimethyl- (8-Hydroxylinalool) 103619-06-32,7-Octadiene-1,6-diol,2,7-dimethyl- 60250-14-8 2-Octene-1,4-diol40735-15-7 2-Octene-1,7-diol 73842-95-22-Octene-1,7-diol,2-methyl-6-methylene- 91140-16-83,5-Octadiene-1,7-diol,3,7-dimethyl- 62875-09-63,5-Octadiene-2,7-diol,2,7-dimethyl- 7177-18-63,5-Octanediol,4-methylene- 143233-15-23,7-Octadiene-1,6-diol,2,6-dimethyl- 127446-29-13,7-Octadiene-2,5-diol,2,7-dimethyl- 171436-39-83,7-Octadiene-2,6-diol,2,6-dimethyl- 150283-67-33-Octene-1,5-diol,4-methyl- 147028-43-1 3-Octene-1,5-diol,5-methyl-19764-77-3 4,6-Octadiene-1,3-diol,2,2-dimethyl- 39824-01-64,7-Octadiene-2,3-diol,2,6-dimethyl 51117-38-54,7-Octadiene-2,6-diol,2,6-dimethyl- 59076-71-04-Octene-1,6-diol,7-methyl- 84538-24-94-Octene-1,8-diol,2,7-bis(methylene)- 109750-56-34-Octene-1,8-diol,2-methylene- 109750-58-55,7-Octadiene-1,4-diol,2,7-dimethyl- 105676-78-65,7-Octadiene-1,4-diol,7-methyl- 105676-80-0 5-Octene-1,3-diol130272-38-7 6-Octene-1,3-diol,7-methyl- 110971-19-26-Octene-1,4-diol,7-methyl- 152715-87-2 6-Octene-1,5-diol 145623-79-66-Octene-1,5-diol,7-methyl- 116214-61-0 6-Octene-3,5-diol,2-methyl-65534-66-9 6-Octene-3,5-diol,4-methyl- 156414-25-47-Octene-1,3-diol,2-methyl- 155295-38-8 7-Octene-1,3-diol,4-methyl-142459-25-4 7-Octene-1,3-diol,7-methyl- 132130-96-2 7-Octene-1,5-diol7310-51-2 7-Octene-1,6-diol 159099-43-1 7-Octene-1,6-diol,5-methyl-144880-56-8 7-Octene-2,4-diol,2-methyl-6-methylene- 72446-81-27-Octene-2,5-diol,7-methyl- 152344-12-2 7-Octene-3,5-diol,2-methyl-98753-85-6 1-Nonene-3,5-diol 119554-56-2 1-Nonene-3,7-diol 23866-97-93-Nonene-2,5-diol 165746-84-9 4,6-Nonadiene-1,3-diol,8-methyl-124099-52-1 4-Nonene-2,8-diol 154600-80-3 6,8-Nonadiene-1,5-diol108586-03-4 7-Nonene-2,4-diol 30625-41-3 8-Nonene-2,4-diol 119785-59-08-Nonene-2,5-diol 132381-58-9 1,9-Decadiene-3,8-diol 103984-04-91,9-Decadiene-4,6-diol 138835-67-3 Preferred Unsaturated Diols1,3-Butanediol)2,2-diallyl- 103985-49-51,3-Butanediol,2-(1-ethyl-1-propenyl)- 116103-35-61,3-Butanediol,2-(2-butenyl)-2-methyl 92207-83-51,3-Butanediol,2-(3-methyl-2-butenyl) 98955-19-21,3-Butanediol,2-ethyl-2-(2-propenyl)- 122761-93-71,3-Butanediol,2-methyl-2-(1-methyl-2-propenyl)- 141585-58-21,4-Butanediol,2,3-bis(1-methylethylidene)- 52127-63-61,3-Pentanediol,2-ethenyl-3-ethyl- 104683-37-61,3-Pentanediol,2-ethenyl-4,4-dimethyl- 143447-08-91,4-Pentanediol,3-methyl-2-(2-propenyl)- 139301-86-34-Pentene-1,3-diol,2-(1,1-dimethylethyl)- 109788-04-74-Pentene-1,3-diol,2-ethyl-2,3-dimethyl- 90676-97-41,4-Hexanediol,4-ethyl-2-methylene- 66950-87-61,5-Hexadiene-3,4-diol,2,3,5-trimethyl- 18984-03-71,5-Hexanediol,2-(1-methylethenyl)- 96802-18-52-Hexene-1,5-diol,4-ethenyl-2,5-dimethyl- 70101-76-71,4-Heptanediol,6-methyl-5-methylene- 100590-29-22,4-Heptadiene-2,6-diol,4,6-dimethyl- 102605-95-82,6-Heptadiene-1,4-diol,2,5,5-trimethyl- 115346-30-02-Heptene-1,4-diol,5,6-dimethyl- 103867-76-13-Heptene-1,5-diol,4,6-dimethyl- 147028-45-35-Heptene-1,3-diol,2,4-dimethyl- 123363-69-95-Heptene-1,3-diol,3,6-dimethyl- 96924-52-65-Heptene-1,4-diol,2,6-dimethyl- 106777-98-45-Heptene-1,4-diol,3,6-dimethyl- 106777-99-56-Heptene-1,3-diol,2,2-dimethyl- 140192-39-86-Heptene-1,4-diol,5,6-dimethyl- 152344-16-66-Heptene-1,5-diol,2,4-dimethyl- 74231-27-96-Heptene-1,5-diol,2-ethylidene-6-methyl- 91139-73-0 6-Heptene-Z4-diol,4-(2-propenyl)- 101536-75-8 1-Octene-3,6-diol,3-ethenyl-65757-34-8 2,4,6-Octatriene-1,8-diol,2,7-dimethyl- 162648-63-72,5-Octadiene-1,7-diol,2,6-dimethyl- 91140-07-72,5-Octadiene-1,7-diol,3,7-dimethyl- 117935-59-82,6-Octadiene-1,4-diol,3,7-dimethyl- (Rosiridol) 101391-01-92,6-Octadiene-1,8-diol,2-methyl- 149112-02-72,7-Octadiene-1,4-diol,3,7-dimethyl- 91140-08-82,7-Octadiene-1,5-diol,2,6-dimethyl- 91140-09-92,7-Octadiene-1,6-diol,2,6-dimethyl- (8-Hydroxylinalool) 103619-06-32,7-Octadiene-1,6-diol,2,7-dimethyl- 60250-14-82-Octene-1,7-diol,2-methyl-6-methylene- 91140-16-83,5-Octadiene-2,7-diol,2,7-dimethyl- 7177-18-63,5-Octanediol,4-methylene- 143233-15-23,7-Octadiene-1,6-diol,2,6-dimethyl- 127446-29-14-Octene-1,8-diol,2-methylene- 109750-58-5 6-Octene-3,5-diol,2-methyl-65534-66-9 6-Octene-3,5-diol,4-methyl- 156414-25-47-Octene-2,4-diol,2-methyl-6-methylene- 72446-81-27-Octene-2,5-diol,7-methyl- 152344-12-2 7-Octene-3,5-diol,2-methyl-98753-85-6 1-Nonene-3,5-diol 119554-56-2 1-Nonene-3,7-diol 23866-97-93-Nonene-2,5-diol 165746-84-9 4-Nonene-2,8-diol 154600-80-36,8-Nonadiene-1,5-diol 108586-03-4 7-Nonene-2,4-diol 30625-41-38-Nonene-2,4-diol 119785-59-0 8-Nonene-2,5-diol 132381-58-91,9-Decadiene-3,8-diol 103984-04-9 1,9-Decadiene-4,6-diol 138835-67-3;

and

XI. mixtures thereof.

There are no C₁₋₂ mono-ols that provide the clear concentrated fabricsoftener compositions of this invention. Only one C₃ mono-ol,n-propanol, provides acceptable performance (forms a clear product andeither keeps it clear to a temperature of about 4° C., or allows it torecover upon rewarming to room temperature), although its boiling point(BP) is undesirably low. Of the C₄ mono-ols, only 2-butanol and2-methyl-2-propanol provide very good performance, but2-methyl-2-propanol has a BP that is undesirably low. There are no C₅₋₆mono-ols that provide clear products except for unsaturated mono-ols asdescribed above and hereinafter.

It is found that some principal solvents which have two hydroxyl groupsin their chemical formulas are suitable for use in the formulation ofthe liquid concentrated, clear fabric softener compositions of thisinvention. It is discovered that the suitability of each principalsolvent is surprisingly very selective, dependent on the number ofcarbon atoms, the isomeric configuration of the molecules having thesame number of carbon atoms, the degree of unsaturation, etc. Principalsolvents with similar solubility characteristics to the principalsolvents above and possessing at least some asymmetry will provide thesame benefit. It is discovered that the suitable principal solvents havea ClogP of from about 0.15 to about 0.64, preferably from about 0.25 toabout 0.62, and more preferably from about 0.40 to about 0.60.

For example, for the 1,2-alkanediol principal solvent series having thegeneral formula HO—CH₂—CHOH—(CH₂)_(n)—H, with n being from 1 to 8, only1,2-hexanediol (n=4), which has a ClogP value of about 0.53, which iswithin the effective ClogP range of from about 0.15 to about 0.64, is agood principal solvent, and is within the claim of this invention, whilethe others, e.g., 1,2-propanediol, 1,2-butanediol, 1,2-pentanediol,1,2-octanediol, 1,2-decanediol, having ClogP values outside theeffective 0.15-0.64 range, are not. Furthermore, of the hexanediolisomers, again, the 1,2-hexanediol is a good principal solvent, whilemany other isomers such as 1,3-hexanediol, 1,4-hexanediol,1,5-hexanediol, 1,6-hexanediol, 2,4-hexanediol, and 2,5-hexanediol,having ClogP values outside the effective 0.15-0.64 range, are not.These are illustrated by the Examples and Comparative Examples I-A andI-B (vide infra).

There are no C₃-C₅ diols that provide a clear concentrated compositionin the context of this invention.

Although there are many C₆ diols that are possible isomers, only theones listed above are suitable for making clear products and only:1,2-butanediol, 2,3-dimethyl-; 1,2-butanediol, 3,3-dimethyl-;2,3-pentanediol, 2-methyl-; 2,3-pentanediol, 3-methyl-; 2,3-pentanediol,4-methyl-; 2,3-hexanediol; 3,4-hexanediol; 1,2-butanediol, 2-ethyl-;1,2-pentanediol, 2-methyl-; 1,2-pentanediol, 3-methyl-; 1,2-pentanediol,4-methyl-; and 1,2-hexanediol are preferred, of which the most preferredare: 1,2-butanediol, 2-ethyl-; 1,2-pentanediol, 2-methyl-;1,2-pentanediol, 3-methyl-; 1,2-pentanediol, 4-methyl-; and1,2-hexanediol.

There are more possible C₇ diol isomers, but only the listed onesprovide clear products and the preferred ones are: 1,3-butanediol,2-butyl-; 1,4-butanediol, 2-propyl-; 1,5-pentanediol, 2-ethyl-;2,3-pentanediol, 2,3-dimethyl-; 2,3-pentanediol, 2,4-dimethyl-;2,3-pentanediol, 4,4-dimethyl-; 3,4-pentanediol, 2,3-dimethyl-;1,6-hexanediol, 2-methyl-; 1,6-hexanediol, 3-methyl-; 1,3-heptanediol;1,4-heptanediol; 1,5-heptanediol; 1,6-heptanediol; of which the mostpreferred are: 2,3-pentanediol, 2,3-dimethyl-; 2,3-pentanediol,2,4-dimethyl-; 2,3-pentanediol, 3,4-dimethyl-; 2,3-pentanediol,4,4-dimethyl-; and 3,4-pentanediol, 2,3-dimethyl-.

Similarly, there are even more C₈ diol isomers, but only the listed onesprovide clear products and the preferred ones are: 1,3-propanediol,2-(1,1-dimethylpropyl)-; 1,3-propanediol, 2-(1,2-dimethylpropyl)-;1,3-propanediol, 2-(1-ethylpropyl)-; 1,3-propanediol,2-(2,2-dimethylpropyl)-; 1,3-propanediol, 2-ethyl-2-isopropyl-;1,3-propanediol, 2-methyl-2-(1-methylpropyl)-; 1,3-propanediol,2-methyl-2-(2-methylpropyl)-; 1,3-propanediol,2-tertiary-butyl-2-methyl-; 1,3-butanediol, 2,2-diethyl; 1,3-butanediol,2-(1-methylpropyl)-; 1,3-butanediol, 2-butyl-; 1,3-butanediol,2-ethyl-2,3-dimethyl-; 1,3-butanediol, 2-(1,1-dimethylethyl)-;1,3-butanediol, 2-(2-methylpropyl)-; 1,3-butanediol, 2-methyl-2-propyl-;1,3-butanediol, 2-methyl-2-isopropyl-; 1,3-butanediol,3-methyl-2-propyl-; 1,4-butanediol, 2,2-diethyl-; 1,4-butanediol,2-ethyl-2,3-dimethyl-; 1,4-butanediol, 2-ethyl-3,3-dimethyl-;1,4-butanediol, 2-(1,1-dimethylethyl)-; 1,4-butanediol,3-methyl-2-isopropyl-; 1,3-pentanediol, 2,2,3-trimethyl-;1,3-pentanediol, 2,2,4-trimethyl-; 1,3-pentanediol, 2,3,4-trimethyl-;1,3-pentanediol, 2,4,4-trimethyl-; 1,3-pentanediol, 3,4,4-trimethyl-;1,4-pentanediol, 2,2,3-trimethyl-; 1,4-pentanediol, 2,2,4-trimethyl-;1,4-pentanediol, 2,3,3-trimethyl-; 1,4-pentanediol, 2,3,4-trimethyl-;1,4-pentanediol, 3,3,4-trimethyl-; 1,5-pentanediol, 2,2,3-trimethyl-;1,5-pentanediol, 2,2,4-trimethyl-; 1,5-pentanediol, 2,3,3-trimethyl-;2,4-pentanediol, 2,3,4-trimethyl-; 1,3-pentanediol, 2-ethyl-2-methyl-;1,3-pentanediol, 2-ethyl-3-methyl-; 1,3-pentanediol, 2-ethyl-4-methyl-;1,3-pentanediol, 3-ethyl-2-methyl-; 1,4-pentanediol, 2-ethyl-2-methyl-;1,4-pentanediol, 2-ethyl-3-methyl-; 1,4-pentanediol, 2-ethyl-4-methyl-;1,5-pentanediol, 3-ethyl-3-methyl-; 2,4-pentanediol, 3-ethyl-2-methyl-;1,3-pentanediol, 2-isopropyl-; 1,3-pentanediol, 2-propyl-;1,4-pentanediol, 2-isopropyl-; 1,4-pentanediol, 2-propyl-;1,4-pentanediol, 3-isopropyl-; 2,4-pentanediol, 3-propyl-1,3-hexanediol,2,2-dimethyl-; 1,3-hexanediol, 2,3-dimethyl-; 1,3-hexanediol,2,4-dimethyl-; 1,3-hexanediol, 2,5-dimethyl-; 1,3-hexanediol,3,4-dimethyl-; 1,3-hexanediol, 3,5-dimethyl-; 1,3-hexanediol,4,4-dimethyl-; 1,3-hexanediol, 4,5-dimethyl-; 1,4-hexanediol,2,2-dimethyl-; 1,4-hexanediol, 2,3-dimethyl-; 1,4-hexanediol,2,4-dimethyl-; 1,4-hexanediol, 2,5-dimethyl-; 1,4-hexanediol,3,3-dimethyl-; 1,4-hexanediol, 3,4-dimethyl-; 1,4-hexanediol,3,5-dimethyl-; 1,4-hexanediol, 4,5-dimethyl-; 1,4-hexanediol,5,5-dimethyl-; 1,5-hexanediol, 2,2-dimethyl-; 1,5-hexanediol,2,3-dimethyl-; 1,5-hexanediol, 2,4-dimethyl-; 1,5-hexanediol,2,5-dimethyl-; 1,5-hexanediol, 3,3-dimethyl-; 1,5-hexanediol,3,4-dimethyl-; 1,5-hexanediol, 3,5-dimethyl-; 1,5-hexanediol,4,5-dimethyl-; 2,6-hexanediol, 3,3-dimethyl-; 1,3-hexanediol, 2-ethyl-;1,3-hexanediol, 4-ethyl-; 1,4-hexanediol, 2-ethyl-; 1,4-hexanediol,4-ethyl-; 1,5-hexanediol, 2-ethyl-; 2,4-hexanediol, 3-ethyl-;2,4-hexanediol, 4-ethyl-; 2,5-hexanediol, 3-ethyl-; 1,3-heptanediol,2-methyl-; 1,3-heptanediol, 3-methyl-; 1,3-heptanediol, 4-methyl-;1,3-heptanediol, 5-methyl-; 1,3-heptanediol, 6-methyl-; 1,4-heptanediol,2-methyl-; 1,4-heptanediol, 3-methyl-; 1,4-heptanediol, 4-methyl-;1,4-heptanediol, 5-methyl-; 1,4-heptanediol, 6-methyl-; 1,5-heptanediol,2-methyl-; 1,5-heptanediol, 3-methyl-; 1,5-heptanediol, 4-methyl-;1,5-heptanediol, 5-methyl-; 1,5-heptanediol, 6-methyl-; 1,6-heptanediol,2-methyl-; 1,6-heptanediol, 3-methyl-; 1,6-heptanediol, 4-methyl-;1,6-heptanediol, 5-methyl-; 1,6-heptanediol, 6-methyl-; 2,4-heptanediol,2-methyl-; 2,4-heptanediol, 3-methyl-; 2,4-heptanediol, 4-methyl-;2,4-heptanediol, 5-methyl-; 2,4-heptanediol, 6-methyl-; 2,5-heptanediol,2-methyl-; 2,5-heptanediol, 3-methyl-; 2,5-heptanediol, 4-methyl-;2,5-heptanediol, 5-methyl-; 2,5-heptanediol, 6-methyl-; 2,6-heptanediol,2-methyl-; 2,6-heptanediol, 3-methyl-; 2,6-heptanediol, 4-methyl-;3,4-heptanediol, 3-methyl-; 3,5-heptanediol, 2-methyl-; 3,5-heptanediol,4-methyl-; 2,4-octanediol; 2,5-octanediol; 2,6-octanediol;2,7-octanediol; 3,5-octanediol; and/or 3,6-octanediol of which thefollowing are the most preferred: 1,3-propanediol,2-(1,1-dimethylpropyl)-; 1,3-propanediol, 2-(1,2-dimethylpropyl)-;1,3-propanediol, 2-(1-ethylpropyl)-; 1,3-propanediol,2-(2,2-dimethylpropyl)-; 1,3-propanediol, 2-ethyl-2-isopropyl-;1,3-propanediol, 2-methyl-2-(1-methylpropyl)-; 1,3-propanediol,2-methyl-2-(2-methylpropyl)-; 1,3-propanediol,2-tertiary-butyl-2-methyl-; 1,3-butanediol, 2-(1-methylpropyl)-;1,3-butanediol, 2-(2-methylpropyl)-; 1,3-butanediol, 2-butyl-;1,3-butanediol, 2-methyl-2-propyl-; 1,3-butanediol, 3-methyl-2-propyl-;1,4-butanediol, 2,2-diethyl-; 1,4-butanediol, 2-ethyl-2,3-dimethyl-;1,4-butanediol, 2-ethyl-3,3-dimethyl-; 1,4-butanediol,2-(1,1-dimethylethyl)-; 1,3-pentanediol, 2,3,4-trimethyl-;1,5-pentanediol, 2,2,3-trimethyl-; 1,5-pentanediol, 2,2,4-trimethyl-;1,5-pentanediol, 2,3,3-trimethyl-; 1,3-pentanediol, 2-ethyl-2-methyl-;1,3-pentanediol, 2-ethyl-3-methyl-; 1,3-pentanediol, 2-ethyl-4-methyl-;1,3-pentanediol, 3-ethyl-2-methyl-; 1,4-pentanediol, 2-ethyl-2-methyl-;1,4-pentanediol, 2-ethyl-3-methyl-; 1,4-pentanediol, 2-ethyl-4-methyl-;1,5-pentanediol, 3-ethyl-3-methyl-; 2,4-pentanediol, 3-ethyl-2-methyl-;1,3-pentanediol, 2-isopropyl-; 1,3-pentanediol, 2-propyl-;1,4-pentanediol, 2-isopropyl-; 1,4-pentanediol, 2-propyl-;1,4-pentanediol, 3-isopropyl-; 2,4-pentanediol, 3-propyl-;1,3-hexanediol, 2,2-dimethyl-; 1,3-hexanediol, 2,3-dimethyl-;1,3-hexanediol, 2,4-dimethyl-; 1,3-hexanediol, 2,5-dimethyl-;1,3-hexanediol, 3,4-dimethyl-; 1,3-hexanediol, 3,5-dimethyl-;1,3-hexanediol, 4,4-dimethyl-; 1,3-hexanediol, 4,5-dimethyl-;1,4-hexanediol, 2,2-dimethyl-; 1,4-hexanediol, 2,3-dimethyl-;1,4-hexanediol, 2,4-dimethyl-; 1,4-hexanediol, 2,5-dimethyl-;1,4-hexanediol, 3,3-dimethyl-; 1,4-hexanediol, 3,4-dimethyl-;1,4-hexanediol, 3,5-dimethyl-; 1,4-hexanediol, 4,5-dimethyl-;1,4hexanediol, 5,5-dimethyl-; 1,5-hexanediol, 2,2-dimethyl-;1,5-hexanediol, 2,3-dimethyl-; 1,5-hexanediol, 2,4-dimethyl-;1,5-hexanediol, 2,5-dimethyl-; 1,5-hexanediol, 3,3-dimethyl-;1,5-hexanediol, 3,4-dimethyl-; 1,5-hexanediol, 3,5-dimethyl-;1,5-hexanediol, 4,5-dimethyl-; 2,6-hexanediol, 3,3-dimethyl-;1,3-hexanediol, 2-ethyl-; 1,3-hexanediol, 4-ethyl-; 1,4-hexanediol,2-ethyl-; 1,4-hexanediol, 4-ethyl-; 1,5-hexanediol, 2-ethyl-;2,4-hexanediol, 3-ethyl-; 2,4-hexanediol, 4-ethyl-; 2,5-hexanediol,3-ethyl-; 1,3-heptanediol, 2-methyl-; 1,3-heptanediol, 3-methyl-;1,3-heptanediol, 4-methyl-; 1,3-heptanediol, 5-methyl-; 1,3-heptanediol,6-methyl-; 1,4-heptanediol, 2-methyl-; 1,4-heptanediol, 3-methyl-;1,4-heptanediol, 4-methyl-; 1,4-heptanediol, 5-methyl-; 1,4-heptanediol,6-methyl-; 1,5-heptanediol, 2-methyl-; 1,5-heptanediol, 3-methyl-;1,5-heptanediol, 4-methyl-; 1,5-heptanediol, 5-methyl-; 1,5-heptanediol,6-methyl-; 1,6-heptanediol, 2-methyl-; 1,6-heptanediol, 3-methyl-;1,6-heptanediol, 4-methyl-; 1,6-heptanediol, 5-methyl-; 1,6-heptanediol,6-methyl-; 2,4-heptanediol, 2-methyl-; 2,4-heptanediol, 3-methyl-;2,4-heptanediol, 4-methyl-; 2,4-heptanediol, 5-methyl-; 2,4-heptanediol,6-methyl-; 2,5-heptanediol, 2-methyl-; 2,5-heptanediol, 3-methyl-;2,5-heptanediol, 4-methyl-; 2,5-heptanediol, 5-methyl-; 2,5-heptanediol,6-methyl-; 2,6-heptanediol, 2-methyl-; 2,6-heptanediol, 3-methyl-;2,6-heptanediol, 4-methyl-; 3,4-heptanediol, 3-methyl-; 3,5-heptanediol,2-methyl-; 3,5-heptanediol, 4-methyl-; 2,4-octanediol; 2,5-octanediol;2,6-octanediol; 2,7-octanediol; 3,5-octanediol; and/or 3,6-octanediol.

Preferred mixtures of eight-carbon-atom-1,3 diols can be formed by thecondensation of mixtures of butyraldehyde, isobutyraldehyde and/ormethyl ethyl ketone (2-butanone), so long as there are at least two ofthese reactants in the reaction mixture, in the presence of highlyalkaline catalyst followed by conversion by hydrogenation to form amixture of eight-carbon-1,3-diols, i.e., a mixture of 8-carbon-1,3-diolsprimarily consisting of: 2,2,4-trimethyl-1,3-pentanediol;2-ethyl-1,3-hexanediol; 2,2-dimethyl-1,3-hexanediol;2-ethyl-4-methyl-1,3-pentanediol; 2-ethyl-3-methyl-1,3-pentanediol;3,5-octanediol; 2,2-dimethyl-2,4-hexanediol; 2-methyl-3,5-heptanediol;and/or 3-methyl-3,5-heptanediol, the level of2,2,4-trimethyl-1,3-pentanediol being less than half of any mixture,possibly along with other minor isomers resulting from condensation onthe methylene group of 2-butanone, when it is present, instead of on themethyl group.

The formulatability, and other properties, such as odor, fluidity,melting point lowering, etc., of some C₆₋₈ diols listed above in TablesII-IV which are not preferred, can be improved by polyalkoxylation.Also, some of the C₃₋₅ diols which are alkoxylated are preferred.Preferred alkoxylated derivatives of the above C₃₋₈ diols [In thefollowing disclosure, “EO” means polyethoxylates, “E_(n)” means—(CH₂CH₂O)_(n)H; Me-E_(n) means methyl-capped polyethoxylates—(CH₂CH₂O)_(n)CH₃; “2(Me-En)” means 2 Me-En groups needed; “PO” meanspolypropoxylates, —(CH(CH₃)CH₂O)_(n)H; “BO” means polybutyleneoxygroups, (CH(CH₂CH₃)CH₂O)_(n)H; and “n-BO” means poly(n-butyleneoxy)groups —(CH₂CH₂CH₂CH₂O)_(n)H.] include:

1. 1,2-propanediol (C3) 2(Me-E₃₋₄); 1,2-propanediol (C3) PO₄;1,2-propanediol, 2-methyl-(C4) (Me-E₈₋₁₀); 1,2-propanediol,2-methyl-(C4) 2(Me-E₁); 1,2-propanediol, 2-methyl-(C4) PO₃;1,3-propanediol (C3) 2(Me-E₈); 1,3-propanediol (C3) PO₆;1,3-propanediol, 2,2-diethyl-(C7) E₄₋₇; 1,3-propanediol,2,2-diethyl-(C7) PO₁; 1,3-propanediol, 2,2-diethyl-(C7) n-BO₂;1,3-propanediol, 2,2-dimethyl-(C5) 2(Me E₁₋₂); 1,3-propanediol,2,2-dimethyl-(C5) PO₄; 1,3-propanediol, 2-(1-methylpropyl)-(C7) E₄₋₇;1,3-propanediol, 2-(1-methylpropyl)-(C7) PO₁; 1,3-propanediol,2-(1-methylpropyl)-(C7) n-BO₂; 1,3-propanediol, 2-(2-methylpropyl)-(C7)E₄₋₇; 1,3-propanediol, 2-(2-methylpropyl)-(C7) PO₁; 1,3-propanediol,2-(2-methylpropyl)-(C7) n-BO₂; 1,3-propanediol, 2-ethyl-(C5) (Me E₉₋₁₀);1,3-propanediol, 2-ethyl-(C5) 2(Me E₁); 1,3-propanediol, 2-ethyl-(C5)PO₃; 1,3-propanediol, 2-ethyl-2-methyl-(C6) (Me E₃₋₆); 1,3-propanediol,2-ethyl-2-methyl-(C6) PO₂; 1,3-propanediol, 2-ethyl-2-methyl-(C6) BO₁;1,3-propanediol, 2-isopropyl-(C6) (Me E₃₋₆); 1,3-propanediol,2-isopropyl-(C6) PO₂; 1,3-propanediol, 2-isopropyl-(C6) BO₁;1,3-propanediol, 2-methyl-(C4) 2(Me E₄₋₅); 1,3-propanediol,2-methyl-(C4) PO₅; 1,3-propanediol, 2-methyl-(C4) BO₂; 1,3-propanediol,2-methyl-2-isopropyl-(C7) E₆₋₉; 1,3-propanediol,2-methyl-2-isopropyl-(C7) PO₁; 1,3-propanediol,2-methyl-2-isopropyl-(C7) n-BO₂₋₃; 1,3-propanediol,2-methyl-2-propyl-(C7) E₄₋₇; 1,3-propanediol, 2-methyl-2-propyl-(C7)PO₁; 1,3-propanediol, 2-methyl-2-propyl-(C7) n-BO₂; 1,3-propanediol,2-propyl-(C6) (Me E₁₋₄); 1,3-propanediol, 2-propyl-(C6) PO₂;

2. 1,2-butanediol (C4) (Me E₆₋₈); 1,2-butanediol (C4) PO₂₋₃;1,2-butanediol (C4) BO₁; 1,2-butanediol, 2,3-dimethyl-(C6) E₂₋₅;1,2-butanediol, 2,3-dimethyl-(C6) n-BO₁; 1,2-butanediol, 2-ethyl-(C6)E₁₋₃; 1,2-butanediol, 2-ethyl-(C6) n-BO₁; 1,2-butanediol, 2-methyl-(C5)(Me E₁₋₂); 1,2-butanediol, 2-methyl-(C5) PO₁; 1,2-butanediol,3,3-dimethyl-(C6) E₂₋₅; 1,2-butanediol, 3,3-dimethyl-(C6) n-BO₁;1,2-butanediol, 3-methyl-(C5) (Me E₁₋₂); 1,2-butanediol, 3-methyl-(C5)PO₁; 1,3-butanediol (C4) 2(Me E₅₋₆); 1,3-butanediol (C4) BO₂;1,3-butanediol, 2,2,3-trimethyl-(C7) (Me E₁₋₃); 1,3-butanediol,2,2,3-trimethyl-(C7) PO₂; 1,3-butanediol, 2,2-dimethyl-(C6) (Me E₆₋₈);1,3-butanediol, 2,2-dimethyl-(C6) PO₃; 1,3-butanediol, 2,3-dimethyl-(C6)(Me E₆₋₈); 1,3-butanediol, 2,3-dimethyl-(C6) PO₃; 1,3-butanediol,2-ethyl-(C6) (Me E₄₋₆); 1,3-butanediol, 2-ethyl-(C6) PO₂₋₃;1,3-butanediol, 2-ethyl-(C6) BO₁; 1,3-butanediol, 2-ethyl-2-methyl-(C7)(Me E₁); 1,3-butanediol, 2-ethyl-2-methyl-(C7) PO₁; 1,3-butanediol,2-ethyl-2-methyl-(C7) n-BO₃; 1,3-butanediol, 2-ethyl-3-methyl-(C7) (MeE₁); 1,3-butanediol, 2-ethyl-3-methyl-(C7) PO₁; 1,3-butanediol,2-ethyl-3-methyl-(C7) n-BO₃; 1,3-butanediol, 2-isopropyl-(C7) (Me E₁);1,3-butanediol, 2-isopropyl-(C7) PO₁; 1,3-butanediol, 2-isopropyl-(C7)n-BO₃; 1,3-butanediol, 2-methyl-(C5) 2(Me E₂₋₃); 1,3-butanediol,2-methyl-(C5) PO₄; 1,3-butanediol, 2-propyl-(C7) E₆₋₈; 1,3-butanediol,2-propyl-(C7) PO₁; 1,3-butanediol, 2-propyl-(C7) n-BO₂₋₃;1,3-butanediol, 3-methyl-(C5) 2(Me E₂₋₃); 1,3-butanediol, 3-methyl-(C5)PO₄; 1,4-butanediol (C4) 2(Me E₃₋₄); 1,4-butanediol (C4) PO₄₋₅;1,4-butanediol, 2,2,3-trimethyl-(C7) E₆₋₉; 1,4-butanediol,2,2,3-trimethyl-(C7) PO₁; 1,4-butanediol, 2,2,3-trimethyl-(C7) n-BO₂₋₃;1,4-butanediol, 2,2-dimethyl-(C6) (Me E₃₋₆); 1,4-butanediol,2,2-dimethyl-(C6) PO₂; 1,4-butanediol, 2,2-dimethyl-(C6) BO₁;1,4-butanediol, 2,3-dimethyl-(C6) (Me E₃₋₆); 1,4-butanediol,2,3-dimethyl-(C6) PO₂; 1,4-butanediol, 2,3-dimethyl-(C6) BO₁;1,4-butanediol, 2-ethyl-(C6) (Me E₁₋₄); 1,4-butanediol, 2-ethyl-(C6)PO₂; 1,4-butanediol, 2-ethyl-2-methyl-(C7) E₄₋₇; 1,4-butanediol,2-ethyl-2-methyl-(C7) PO₁; 1,4-butanediol, 2-ethyl-2-methyl-(C7) n-BO₂;1,4-butanediol, 2-ethyl-3-methyl-(C7) E₄₋₇; 1,4-butanediol,2-ethyl-3-methyl-(C7) PO₁; 1,4-butanediol, 2-ethyl-3-methyl-(C7) n-BO₂;1,4-butanediol, 2-isopropyl-(C7) E₄₋₇; 1,4-butanediol, 2-isopropyl-(C7)PO₁; 1,4-butanediol, 2-isopropyl-(C7) n-BO₂; 1,4-butanediol,2-methyl-(C5) (Me E₉₋₁₀); 1,4-butanediol, 2-methyl-(C5) 2(Me E₁);1,4-butanediol, 2-methyl-(C5) PO₃; 1,4-butanediol, 2-propyl-(C7) E₂₋₅;1,4-butanediol, 2-propyl-(C7) n-BO₁; 1,4-butanediol,3-ethyl-1-methyl-(C7) E₆₋₈; 1,4-butanediol, 3-ethyl-1-methyl-(C7) PO₁;1,4-butanediol, 3-ethyl-1-methyl-(C7) n-BO₂₋₃; 2,3-butanediol (C4) (MeE₉₋₁₀); 2,3-butanediol (C4) 2(Me E₁); 2,3-butanediol (C4) PO₃₋₄;2,3-butanediol, 2,3-dimethyl-(C6) E₇₋₉; 2,3-butanediol,2,3-dimethyl-(C6) PO₁; 2,3-butanediol, 2,3-dimethyl-(C6) BO₂₋₃;2,3-butanediol, 2-methyl-(C5) (Me E₂₋₅); 2,3-butanediol, 2-methyl-(C5)PO₂; 2,3-butanediol, 2-methyl-(C5) BO₁;

3. 1,2-pentanediol (C5) E₇₋₁₀; 1,2-pentanediol, (C5) PO₁;1,2-pentanediol, (C5) n-BO₃; 1,2-pentanediol, 2-methyl (C6) E₁₋₃;1,2-pentanediol, 2-methyl (C6) n-BO₁; 1,2-pentanediol, 3-methyl (C6)E₁₋₃; 1,2-pentanediol, 3-methyl (C6) n-BO₁; 1,2-pentanediol, 4-methyl(C6) E₁₋₃; 1,2-pentanediol, 4-methyl (C6) n-BO₁; 1,3-pentanediol (C5)2(Me-E₁₋₂); 1,3-pentanediol (C5) PO₃₋₄; 1,3-pentanediol,2,2-dimethyl-(C7) (Me-E₁); 1,3-pentanediol, 2,2-dimethyl-(C7) PO₁;1,3-pentanediol, 2,2-dimethyl-(C7) n-BO₃; 1,3-pentanediol,2,3-dimethyl-(C7) (Me-E₁); 1,3-pentanediol, 2,3-dimethyl-(C7) PO₁;1,3-pentanediol, 2,3-dimethyl-(C7) n-BO₃; 1,3-pentanediol,2,4-dimethyl-(C7) (Me-E₁); 1,3-pentanediol, 2,4-dimethyl-(C7) PO₁;1,3-pentanediol, 2,4-dimethyl-(C7) n-BO₃; 1,3-pentanediol, 2-ethyl-(C7)E₆₋₈; 1,3-pentanediol, 2-ethyl-(C7) PO₁; 1,3-pentanediol, 2-ethyl-(C7)n-BO₂₋₃; 1,3-pentanediol, 2-methyl-(C6) 2(Me-E₄₋₆); 1,3-pentanediol,2-methyl-(C6) PO₂₋₃; 1,3-pentanediol, 3,4-dimethyl-(C7) (Me-E₁);1,3-pentanediol, 3,4-dimethyl-(C7) PO₁; 1,3-pentanediol,3,4-dimethyl-(C7) n-BO₃; 1,3-pentanediol, 3-methyl-(C6) 2(Me-E₄₋₆);1,3-pentanediol, 3-methyl-(C6) PO₂₋₃; 1,3-pentanediol, 4,4-dimethyl-(C7)(Me-E₁); 1,3-pentanediol, 4,4-dimethyl-(C7) PO₁; 1,3-pentanediol,4,4-dimethyl-(C7) n-BO₃; 1,3-pentanediol, 4-methyl-(C6) 2(Me-E₄₋₆);1,3-pentanediol, 4-methyl-(C6) PO₂₋₃; 1,4-pentanediol, (C5) 2(Me-E₁₋₂);1,4-pentanediol (C5) PO₃₋₄; 1,4-pentanediol, 2,2-dimethyl-(C7) (Me-E₁);1,4-pentanediol, 2,2-dimethyl-(C7) PO₁; 1,4-pentanediol,2,2-dimethyl-(C7) n-BO₃; 1,4-pentanediol, 2,3-dimethyl-(C7) (Me-E₁);1,4-pentanediol, 2,3-dimethyl-(C7) PO₁; 1,4-pentanediol,2,3-dimethyl-(C7) n-BO₃; 1,4-pentanediol, 2,4-dimethyl-(C7) (Me-E₁);1,4-pentanediol, 2,4-dimethyl-(C7) PO₁; 1,4-pentanediol,2,4-dimethyl-(C7) n-BO₃; 1,4-pentanediol, 2-methyl-(C6) (Me-E₄₋₆);1,4-pentanediol, 2-methyl-(C6) PO₂₋₃; 1,4-pentanediol, 3,3-dimethyl-(C7)(Me-E₁); 1,4-pentanediol, 3,3-dimethyl-(C7) PO₁; 1,4-pentanediol,3,3-dimethyl-(C7) n-BO₃; 1,4-pentanediol, 3,4-dimethyl-(C7) (Me-E₁);1,4-pentanediol, 3,4-dimethyl-(C7) PO₁; 1,4-pentanediol,3,4-dimethyl-(C7) n-BO₃; 1,4-pentanediol, 3-methyl-(C6) 2(Me-E₄₋₆);1,4-pentanediol, 3-methyl-(C6) PO₂₋₃; 1,4-pentanediol, 4-methyl-(C6)2(Me-E₄₋₆); 1,4-pentanediol, 4-methyl-(C6) PO₂₋₃; 1,5-pentanediol, (C5)(Me-E₈₋₁₀); 1,5-pentanediol (C5) 2(Me-E₁); 1,5-pentanediol (C5) PO₃;1,5-pentanediol, 2,2-dimethyl-(C7) E₄₋₇; 1,5-pentanediol,2,2-dimethyl-(C7) PO₁; 1,5-pentanediol, 2,2-dimethyl-(C7) n-BO₂;1,5-pentanediol, 2,3-dimethyl-(C7) E₄₋₇; 1,5-pentanediol,2,3-dimethyl-(C7) PO₁; 1,5-pentanediol, 2,3-dimethyl-(C7) n-BO₂;1,5-pentanediol, 2,4-dimethyl-(C7) E₄₋₇; 1,5-pentanediol,2,4-dimethyl-(C7) PO₁; 1,5-pentanediol, 2,4-dimethyl-(C7) n-BO₂;1,5-pentanediol, 2-ethyl-(C7) E_(2-5; 1,5)-pentanediol, 2-ethyl-(C7)n-BO₁; 1,5-pentanediol, 2-methyl-(C6) (Me-E₁₋₄); 1,5-pentanediol,2-methyl-(C6) PO₂; 1,5-pentanediol, 3,3-dimethyl-(C7) E₄₋₇;1,5-pentanediol, 3,3-dimethyl-(C7) PO₁; 1,5-pentanediol,3,3-dimethyl-(C7) n-BO₂; 1,5-pentanediol, 3-methyl-(C6) (Me-E₄);1,5-pentanediol, 3-methyl-(C6) PO₂; 2,3-pentanediol, (C5) (Me-E₁₋₃);2,3-pentanediol, (C5) PO₂; 2,3-pentanediol, 2-methyl-(C6) E₄₋₇;2,3-pentanediol, 2-methyl-(C6) PO₁; 2,3-pentanediol, 2-methyl-(C6)n-BO₂; 2,3-pentanediol, 3-methyl-(C6) E₄₋₇; 2,3-pentanediol,3-methyl-(C6) PO₁; 2,3-pentanediol, 3-methyl-(C6) n-BO₂;2,3-pentanediol, 4-methyl-(C6) E₄₋₇; 2,3-pentanediol, 4-methyl-(C6) PO₁;2,3-pentanediol, 4-methyl-(C6) n-BO₂; 2,4-pentanediol, (C5) 2(Me-E₂₋₄);2,4-pentanediol (C5) PO₄; 2,4-pentanediol, 2,3-dimethyl-(C7) (Me-E₂₋₄);2,4-pentanediol, 2,3-dimethyl-(C7) PO₂; 2,3pentanediol,2,4-dimethyl-(C7) (Me-E₂₋₄); 2,4-pentanediol, 2,4-dimethyl-(C7) PO₂;2,4-pentanediol, 2-methyl-(C7) (Me-E₈₋₁₀); 2,4-pentanediol,2-methyl-(C7) PO₃; 2,4-pentanediol, 3,3-dimethyl-(C7) (Me-E₂₋₄);2,4-pentanediol, 3,3-dimethyl-(C7) PO₂; 2,4-pentanediol, 3-methyl-(C6)(Me-E₈₋₁₀); 2,4-pentanediol, 3-methyl-(C6) PO₃;

4. 1,3-hexanediol (C6) (Me-E₂₋₅); 1,3-hexanediol (C6) PO₂;1,3-hexanediol (C6) BO₁; 1,3-hexanediol, 2-methyl-(C7) E₆₋₈;1,3-hexanediol, 2-methyl-(C7) PO₁; 1,3-hexanediol, 2-methyl-(C7)n-BO₂₋₃; 1,3-hexanediol, 3-methyl-(C7) E₆₋₈; 1,3-hexanediol,3-methyl-(C7) PO₁; 1,3-hexanediol, 3-methyl-(C7) n-BO₂₋₃;1,3-hexanediol, 4-methyl-(C7) E₆₋₈; 1,3-hexanediol, 4-methyl-(C7) PO₁;1,3-hexanediol, 4-methyl-(C7) n-BO₂₋₃; 1,3-hexanediol, 5-methyl-(C7)E₆₋₈; 1,3-hexanediol, 5-methyl-(C7) PO₁; 1,3-hexanediol, 5-methyl-(C7)n-BO₂₋₃; 1,4-hexanediol (C6) (Me-E₂₋₅); 1,4-hexanediol (C6) PO₂;1,4-hexanediol (C6) BO₁; 1,4-hexanediol, 2-methyl-(C7) E₆₋₈;1,4-hexanediol, 2-methyl-(C7) PO₁; 1,4-hexanediol, 2-methyl-(C7)n-BO₂₋₃; 1,4-hexanediol, 3-methyl-(C7) E₆₋₈; 1,4-hexanediol,3-methyl-(C7) PO₁; 1,4-hexanediol, 3-methyl-(C7) n-BO₂₋₃;1,4-hexanediol, 4-methyl-(C7) E₆₋₈; 1,4-hexanediol, 4-methyl-(C7) PO₁;1,4-hexanediol, 4-methyl-(C7) n-BO₂₋₃; 1,4-hexanediol, 5-methyl-(C7)E₆₋₈; 1,4-hexanediol, 5-methyl-(C7) PO₁; 1,4-hexanediol, 5-methyl-(C7)n-BO₂₋₃; 1,5-hexanediol (C6) (Me-E₂₋₅); 1,5-hexanediol (C6) PO₂;1,5-hexanediol (C6) BO₁; 1,5-hexanediol, 2-methyl-(C7) E₆₋₈;1,5-hexanediol, 2-methyl-(C7) PO₁; 1,5-hexanediol, 2-methyl-(C7)n-BO₂₋₃; 1,5-hexanediol, 3-methyl-(C7) E₆₋₈; 1,5-hexanediol,3-methyl-(C7) PO₁; 1,5-hexanediol, 3-methyl-(C7) n-BO₂₋₃;1,5-hexanediol, 4-methyl-(C7) E₆₋₈; 1,5-hexanediol, 4-methyl-(C7) PO₁;1,5-hexanediol, 4-methyl-(C7) n-BO₂₋₃; 1,5-hexanediol, 5-methyl-(C7)E₆₋₈; 1,5-hexanediol, 5-methyl-(C7) PO₁; 1,5-hexanediol, 5-methyl-(C7)n-BO₂₋₃; 1,6-hexanediol (C6) (Me-E₁₋₂); 1,6-hexanediol (C6) PO₂;1,6-hexanediol (C6) n-BO₄; 1,6-hexanediol, 2-methyl-(C7) E₂₋₅;1,6-hexanediol, 2-methyl-(C7) n-BO₁; 1,6-hexanediol, 3-methyl-(C7) E₂₋₅;1,6-hexanediol, 3-methyl-(C7) n-BO₁; 2,3-hexanediol (C6) E₂₋₅;2,3-hexanediol (C6) n-BO₁; 2,4-hexanediol (C6) (Me-E₅₋₈); 2,4-hexanediol(C6) PO₃; 2,4-hexanediol, 2-methyl-(C7) (Me-E₁₋₂); 2,4-hexanediol2-methyl-(C7) PO₁₋₂; 2,4-hexanediol, 3-methyl-(C7) (Me-E₁₋₂);2,4-hexanediol 3-methyl-(C7) PO₁₋₂; 2,4-hexanediol, 4-methyl-(C7)(Me-E₁₋₂); 2,4-hexanediol 4-methyl-(C7) PO₁₋₂; 2,4-hexanediol,5-methyl-(C7) (Me-E₁₋₂); 2,4-hexanediol 5-methyl-(C7) PO₁₋₂;2,5-hexanediol (C6) (Me-E₅₋₈); 2,5-hexanediol (C6) PO₃; 2,5-hexanediol,2-methyl-(C7) (Me-E₁₋₂); 2,5-hexanediol 2-methyl-(C7) PO₁₋₂;2,5-hexanediol, 3-methyl-(C7) (Me-E₁₋₂); 2,5-hexanediol 3-methyl-(C7)PO₁₋₂; 3,4-hexanediol (C6) EO₂₋₅; 3,4-hexanediol (C6) n-BO₁;

5. 1,3-heptanediol (C7) E₃₋₆; 1,3-heptanediol (C7) PO₁; 1,3-heptanediol(C7) n-BO₂; 1,4-heptanediol (C7) E₃₋₆; 1,4-heptanediol (C7) PO₁;1,4-heptanediol (C7) n-BO₂; 1,5-heptanediol (C7) E₃₋₆; 1,5-heptanediol(C7) PO₁; 1,5-heptanediol (C7) n-BO₂; 1,6-heptanediol (C7) E₃₋₆;1,6-heptanediol (C7) PO₁; 1,6-heptanediol (C7) n-BO₂; 1,7-heptanediol(C7) E₁₋₂; 1,7-heptanediol (C7) n-BO₁; 2,4-heptanediol (C7) E₇₋₁₀;2,4-heptanediol (C7) (Me-E₁); 2,4-heptanediol (C7) PO₁; 2,4-heptanediol(C7) n-BO₃; 2,5-heptanediol (C7) E₇₋₁₀; 2,5-heptanediol (C7) (Me-E₁);2,5-heptanediol (C7) PO₁; 2,5-heptanediol (C7) n-BO₃; 2,6-heptanediol(C7) E₇₋₁₀; 2,6-heptanediol (C7) (Me-E₁); 2,6-heptanediol (C7) PO₁;2,6-heptanediol (C7) n-BO₃; 3,5-heptanediol (C7) E₇₋₁₀; 3,5-heptanediol(C7) (Me-E₁); 3,5-heptanediol (C7) PO₁; 3,5-heptanediol (C7) n-BO₃;

6. 1,3-butanediol, 3-methyl-2-isopropyl-(C8) PO₁; 2,4-pentanediol,2,3,3-trimethyl-(C8) PO₁; 1,3-butanediol, 2,2-diethyl-(C8) E₂₋₅;2,4-hexanediol, 2,3-dimethyl-(C8) E₂₋₅; 2,4-hexanediol,2,4-dimethyl-(C8) E₂₋₅; 2,4-hexanediol, 2,5-dimethyl-(C8) E₂₋₅;2,4-hexanediol, 3,3-dimethyl-(C8) E₂₋₅; 2,4-hexanediol,3,4-dimethyl-(C8) E₂₋₅; 2,4-hexanediol, 3,5-dimethyl-(C8) E₂₋₅;2,4-hexanediol 4,5-dimethyl-(C8) E₂₋₅; 2,4-hexanediol, 5,5-dimethyl-(C8)E₂₋₅; 2,5-hexanediol, 2,3-dimethyl-(C8) E₂₋₅; 2,5-hexanediol,2,4-dimethyl-(C8) E₂₋₅; 2,5-hexanediol, 2,5-dimethyl-(C8) E₂₋₅;2,5-hexanediol, 3,3-dimethyl-(C8) E₂₋₅; 2,5-hexanediol,3,4-dimethyl-(C8) E₂₋₅; 3,5-heptanediol, 3-methyl-(C8) E₂₋₅;1,3-butanediol, 2,2-diethyl-(C8) n-BO₁₋₂; 2,4-hexanediol,2,3-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol, 2,4-dimethyl-(C8) n-BO₁₋₂;2,4-hexanediol, 2,5-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol,3,3-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol, 3,4-dimethyl-(C8) n-BO₁₋₂;2,4-hexanediol, 3,5-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol,4,5-dimethyl-(C8) n-BO₁₋₂; 2,4-hexanediol, 5,5-dimethyl-, n-BO₁₋₂;2,5-hexanediol, 2,3-dimethyl-(C8) n-BO₁₋₂; 2,5-hexanediol,2,4-dimethyl-(C8) n-BO₁₋₂; 2,5-hexanediol, 2,5-dimethyl-(C8) n-BO₁₋₂;2,5-hexanediol, 3,3-dimethyl-(C8) n-BO₁₋₂; 2,5-hexanediol,3,4-dimethyl-(C8) n-BO₁₋₂; 3,5-heptanediol, 3-methyl-(C8) n-BO₁₋₂;1,3-propanediol, 2-(1,2-dimethylpropyl)-(C8) n-BO₁; 1,3-butanediol,2-ethyl-2,3-dimethyl-(C8) n-BO₁; 1,3-butanediol,2-methyl-2-isopropyl-(C8) n-BO₁; 1,4-butanediol,3-methyl-2-isopropyl-(C8) n-BO₁; 1,3-pentanediol, 2,2,3-trimethyl-(C8)n-BO₁; 1,3-pentanediol, 2,2,4-trimethyl-(C8) n-BO₁; 1,3-pentanediol,2,4,4-trimethyl-(C8) n-BO₁; 1,3-pentanediol, 3,4,4-trimethyl-(C8) n-BO₁;1,4-pentanediol, 2,2,3-trimethyl-(C8) n-BO₁; 1,4-pentanediol,2,2,4-trimethyl-(C8) n-BO₁; 1,4-pentanediol, 2,3,3-trimethyl-(C8) n-BO₁;1,4-pentanediol, 2,3,4-trimethyl-(C8) n-BO₁; 1,4-pentanediol,3,3,4-trimethyl-(C8) n-BO₁; 2,4-pentanediol, 2,3,4-trimethyl-(C8) n-BO₁;2,4-hexanediol, 4-ethyl-(C8) n-BO₁; 2,4-heptanediol, 2-methyl-(C8)n-BO₁; 2,4-heptanediol, 3-methyl-(C8) n-BO₁; 2,4-heptanediol,4-methyl-(C8) n-BO₁; 2,4-heptanediol, 5-methyl-(C8) n-BO₁;2,4-heptanediol, 6-methyl-(C8) n-BO₁; 2,5-heptanediol, 2-methyl-(C8)n-BO₁; 2,5-heptanediol, 3-methyl-(C8) n-BO₁; 2,5-heptanediol,4-methyl-(C8) n-BO₁; 2,5-heptanediol, 5-methyl-(C8) n-BO₁;2,5-heptanediol, 6-methyl-(C8) n-BO₁; 2,6-heptanediol, 2-methyl-(C8)n-BO₁; 2,6-heptanediol, 3-methyl-(C8) n-BO₁; 2,6-heptanediol,4-methyl-(C8) n-BO₁; 3,5-heptanediol, 2-methyl-(C8) n-BO₁;1,3-propanediol, 2-(1,2-dimethylpropyl)-(C8) E₁₋₃; 1,3-butanediol,2-ethyl-2,3-dimethyl-(C8) E₁₋₃; 1,3-butanediol,2-methyl-2-isopropyl-(C8) E₁₋₃; 1,4-butanediol,3-methyl-2-isopropyl-(C8) E₁₋₃; 1,3-pentanediol, 2,2,3-trimethyl-(C8)E₁₋₃; 1,3-pentanediol, 2,2,4-trimethyl-(C8) E₁₋₃; 1,3-pentanediol,2,4,4-trimethyl-(C8) E₁₋₃; 1,3-pentanediol, 3,4,4-trimethyl-(C8) E₁₋₃;1,4-pentanediol, 2,2,3-trimethyl-(C8) E₁₋₃; 1,4-pentanediol,2,2,4-trimethyl-(C8) E₁₋₃; 1,4-pentanediol, 2,3,3-trimethyl-(C8) E₁₋₃;1,4-pentanediol, 2,3,4-trimethyl-(C8) E₁₋₃; 1,4-pentanediol,3,3,4-trimethyl-(C8) E₁₋₃; 2,4-pentanediol, 2,3,4-trimethyl-(C8) E₁₋₃;2,4-hexanediol, 4-ethyl-(C8) E₁₋₃; 2,4-heptanediol, 2-methyl-(C8) E₁₋₃;2,4-heptanediol, 3-methyl-(C8) E₁₋₃; 2,4-heptanediol, 4-methyl-(C8)E₁₋₃; 2,4-heptanediol, 5-methyl-(C8) E₁₋₃; 2,4-heptanediol,6-methyl-(C8) E₁₋₃; 2,5-heptanediol, 2-methyl-(C8) E₁₋₃;2,5-heptanediol, 3-methyl-(C8) E₁₋₃; 2,5-heptanediol, 4-methyl-(C8)E₁₋₃; 2,5-heptanediol, 5-methyl-(C8) E₁₋₃; 2,5-heptanediol,6-methyl-(C8) E₁₋₃; 2,6-heptanediol, 2-methyl-(C8) E₁₋₃;2,6-heptanediol, 3-methyl-(C8) E₁₋₃; 2,6-heptanediol, 4-methyl-(C8)E₁₋₃; and/or 3,5-heptanediol, 2-methyl-(C8) E₁₋₃; and

7. mixtures thereof

Of the nonane isomers, only 2,4-pentadiol, 2,3,3,4-tetramethyl- ishighly preferred.

In addition to the aliphatic diol principal solvents, and some of theiralkoxylated derivatives, discussed hereinbefore and hereinafter, somespecific diol ethers are also found to be suitable principal solventsfor the formulation of liquid concentrated, clear fabric softenercompositions of the present invention. Similar to the aliphatic diolprincipal solvents, it is discovered that the suitability of eachprincipal solvent is very selective, depending, e.g., on the number ofcarbon atoms in the specific diol ether molecules. For example, as givenin Table VI, for the glyceryl ether series having the formulaHOCH₂—CHOH—CH₂—O—R, wherein R is from C2 to C8 alkyl, only monopentylethers with the formula HOCH₂—CHOH—CH₂—O—C₅H₁₁(3-pentyloxy-1,2-propanediol), wherein the C₅H₁₁ group comprisesdifferent pentyl isomers, have ClogP values within the preferred ClogPvalues of from about 0.25 to about 0.62 and are suitable for theformulation of liquid concentrated, clear fabric softeners of thepresent invention. These are illustrated by the Examples and ComparativeExamples XXXIIA-7 to XXXIIA-7F. It is also found that the cyclohexylderivative, but not the cyclopentyl derivative, is suitable. Similarly,selectivity is exhibited in the selection of aryl glyceryl ethers. Ofthe many possible aromatic groups, only a few phenol derivatives aresuitable.

The same narrow selectivity is also found for the di(hydroxyalkyl)ethers. It is discovered that bis(2-hydroxybutyl) ether, but notbis(2-hydroxypentyl) ether, is suitable. For the di(cyclic hydroxyalkyl)analogs, the bis(2-hydroxycyclopentyl) ether is suitable, but not thebis(2-hydroxycyclohexyl) ether. Non-limiting examples of synthesismethods for the preparation of some preferred di(hydroxyalkyl) ethersare given hereinafter.

The butyl monoglycerol ether (also named 3-butyloxy-1,2-propanediol) isnot well suited to form liquid concentrated, clear fabric softeners ofthe present invention. However, its polyethoxylated derivatives,preferably from about triethoxylated to about nonaethoxylated, morepreferably from pentaethoxylated to octaethoxylated, are suitableprincipal solvents, as given in Table VI.

All of the preferred alkyl glyceryl ethers and/or di(hydroxyalkyl)ethersthat have been identified are given in Table VI and the most preferredare: 1,2-propanediol, 3-(n-pentyloxy)-; 1,2-propanediol,3-(2-pentyloxy)-; 1,2-propanediol, 3-(3-pentyloxy)-; 1,2-propanediol,3-(2-methyl-1-butyloxy)-; 1,2-propanediol, 3-(iso-amyloxy)-;1,2-propanediol, 3-(3-methyl-2-butyloxy)-; 1,2-propanediol,3-(cyclohexyloxy)-; 1,2-propanediol, 3-(1-cyclohex-1-enyloxy)-;1,3-propanediol, 2-(pentyloxy)-; 1,3-propanediol, 2-(2-pentyloxy)-;1,3-propanediol, 2-(3-pentyloxy)-; 1,3-propanediol,2-(2-methyl-1-butyloxy)-; 1,3-propanediol, 2-(iso-amyloxy)-;1,3-propanediol, 2-(3-methyl-2-butyloxy)-; 1,3-propanediol,2-(cyclohexyloxy)-; 1,3-propanediol, 2-(1-cyclohex-1-enyloxy)-;1,2-propanediol, 3-(butyloxy)-, pentaethoxylated; 1,2-propanediol,3-(butyloxy)-, hexaethoxylated; 1,2-propanediol, 3-(butyloxy)-,heptaethoxylated; 1,2-propanediol, 3-(butyloxy)-, octaethoxylated;1,2-propanediol, 3-(butyloxy)-, nonaethoxylated; 1,2-propanediol,3-(butyloxy)-, monopropoxylated; 1,2-propanediol, 3-(butyloxy)-,dibutyleneoxylated; and/or 1,2-propanediol, 3-(butyloxy)-,tributyleneoxylated. Preferred aromatic glyceryl ethers include:1,2-propanediol, 3-phenyloxy-; 1,2-propanediol, 3-benzyloxy-;1,2-propanediol, 3-(2-phenylethyloxy)-; 1,2-propanediol,1,3-propanediol, 2-(m-cresyloxy); 1,3-propanediol, 2-(p-cresyloxy)-;1,3-propanediol, 2-benzyloxy-; 1,3-propanediol, 2-(2-phenylethyloxy)-;and mixtures thereof. The more preferred aromatic glyceryl ethersinclude: 1,2-propanediol, 3-phenyloxy-; 1,2-propanediol, 3-benzyloxy-;1,2-propanediol, 3-(2-phenylethyloxy)-; 1,2-propanediol,1,3-propanediol, 2-(m-cresyloxy)-; 1,3-propanediol, 2-(p-cresyloxy)-;1,3-propanediol, 2-(2-phenylethyloxy)-; and mixtures thereof. The mostpreferred di(hydroxyalkyl)ethers include: bis(2-hydroxybutyl)ether; andbis(2-hydroxycyclopentyl)ether;

Non-limiting example of synthesis methods to prepare the preferred alkyland aryl monoglyceryl ethers is given in the copending application Ser.No. 08/679,694, incorporated hereinbefore by reference.

The alicyclic diols and their derivatives that are preferred include:(1) the saturated diols and their derivatives including:1-isopropyl-1,2-cyclobutanediol; 3-ethyl-4-methyl-1,2-cyclobutanediol;3-propyl-12-cyclobutanediol; 3-isopropyl-1,2-cyclobutanediol;1-ethyl-1,2-cyclopentanediol; 1,2-dimethyl-1,2-cyclopentanediol;1,4-dimethyl-1,2-cyclopentanediol; 2,4,5-trimethyl-1,3-cyclopentanediol;3,3-dimethyl-1,2-cyclopentanediol; 3,4-dimethyl-1,2-cyclopentanediol;3,5-dimethyl-1,2-cyclopentanediol; 3-ethyl-1,2-cyclopentanediol;4,4-dimethyl-1,2-cyclopentanediol; 4-ethyl-1,2-cyclopentanediol;1,1-bis(hydroxymethyl)cyclohexane; 1,2-bis(hydroxymethyl)cyclohexane;1,2-dimethyl-1,3-cyclohexanediol; 1,3-bis(hydroxymethyl)cyclohexane;1,3-dimethyl-1,3-cyclohexanediol; 1,6-dimethyl-1,3-cyclohexanediol;1-hydroxy-cyclohexaneethanol; 1-hydroxy-cyclohexanemethanol;1-ethyl-1,3-cyclohexanediol; 1-methyl-1,2-cyclohexanediol;2,2-dimethyl-1,3-cyclohexanediol; 2,3-dimethyl-1,4-cyclohexanediol;2,4-dimethyl-1,3-cyclohexanediol; 2,5-dimethyl-1,3-cyclohexanediol;2,6-dimethyl-1,4-cyclohexanediol; 2-ethyl-1,3-cyclohexanediol;2-hydroxycyclohexaneethanol; 2-hydroxyethyl-1-cyclohexanol;2-hydroxymethylcyclohexanol; 3-hydroxyethyl-1-cyclohexanol;3-hydroxycyclohexaneethanol; 3-hydroxymethylcyclohexanol;3-methyl-1,2-cyclohexanediol; 4,4-dimethyl-1,3-Cyclohexanediol;4,5-dimethyl-1,3-cyclohexanediol; 4,6-dimethyl-1,3-cyclohexanediol;4-ethyl-1,3-cyclohexanediol; 4-hydroxyethyl-1-cyclohexanol;4-hydroxymethylcyclohexanol; 4-methyl-1,2-cyclohexanediol;5,5-dimethyl-1,3-cyclohexanediol; 5-ethyl-1,3-cyclohexanediol;1,2-cycloheptanediol; 2-methyl-1,3-cycloheptanediol;2-methyl-1,4-cycloheptanediol; 4-methyl-1,3-cycloheptanediol;5-methyl-1,3-cycloheptanediol; 5-methyl-1,4-cycloheptanediol;6-methyl-1,4-cycloheptanediol; 1,3-cyclooctanediol; 1,4-cyclooctanediol;1,5-cyclooctanediol; 1,2-cyclohexanediol, diethoxylate;1,2-cyclohexanediol, triethoxylate; 1,2-cyclohexanediol,tetraethoxylate; 1,2-cyclohexanediol, pentaethoxylate;1,2-cyclohexanediol, hexaethoxylate; 1,2-cyclohexanediol,heptaethoxylate; 1,2-cyclohexanediol, octaethoxylate;1,2-cyclohexanediol, nonaethoxylate; 1,2-cyclohexanediol,monopropoxylate; 1,2-cyclohexanediol, monobutylenoxylate;1,2-cyclohexanediol, dibutylenoxylate; and/or 1,2-cyclohexanediol,tributylenoxylate. The most preferred saturated alicyclic diols andtheir derivatives are: 1-isopropyl-1,2-cyclobutanediol;3-ethyl-4-methyl-1,2-cyclobutanediol; 3-propyl-1,2-cyclobutanediol;3-isopropyl-1,2-cyclobutanediol; 1-ethyl-1,2-cyclopentanediol;1,2-dimethyl-1,2-cyclopentanediol; 1,4-dimethyl-1,2-cyclopentanediol;3,3-dimethyl-1,2-cyclopentanediol; 3,4-dimethyl-1,2-cyclopentanediol;3,5-dimethyl-1,2-cyclopentanediol; 3-ethyl-1,2-cyclopentanediol;4,4-dimethyl-1,2-cyclopentanediol; 4-ethyl-1,2-cyclopentanediol;1,1-bis(hydroxymethyl)cyclohexane; 1,2-bis(hydroxymethyl)cyclohexane;1,2-dimethyl-1,3-cyclohexanediol; 1,3-bis(hydroxymethyl)cyclohexane;1-hydroxycyclohexanemethanol; 1-methyl-1,2-cyclohexanediol;3-hydroxymethylcyclohexanol; 3-methyl-1,2-cyclohexanediol;4,4-dimethyl-1,3-cyclohexanediol; 4,5-dimethyl-1,3-cyclohexanediol;4,6-dimethyl-1,3-cyclohexanediol; 4-ethyl-1,3-cyclohexanediol;4-hydroxyethyl-1-cyclohexanol; 4-hydroxymethylcyclohexanol;4-methyl-1,2-cyclohexanediol; 1,2-cycloheptanediol; 1,2-cyclohexanediol,pentaethoxylate; 1,2-cyclohexanediol, hexaethoxylate;1,2-cyclohexanediol, heptaethoxylate; 1,2-cyclohexanediol,octaethoxylate; 1,2-cyclohexanediol, nonaethoxylate;1,2-cyclohexanediol, monopropoxylate; and/or 1,2-cyclohexanediol,dibutylenoxylate.

Preferred aromatic diols include: 1-phenyl-1,2-ethanediol;1-phenyl-1,2-propanediol; 2-phenyl-1,2-propanediol;3-phenyl-1,2-propanediol; 1-(3-methylphenyl)-1,3-propanediol;1-(4-methylphenyl)-1,3-propanediol; 2-methyl-1-phenyl-1,3-propanediol;1-phenyl-1,3-butanediol; 3-phenyl-1,3-butanediol; and/or1-phenyl-1,4-butanediol, of which, 1-phenyl-1,2-propanediol;2-phenyl-1,2-propanediol; 3-phenyl-1,2-propanediol;1-(3-methylphenyl)-1,3-propanediol; 1-(4-methylphenyl)-1,3-propanediol;2-methyl-1-phenyl-1,3-propanediol; and/or 1-phenyl-1,4-butanediol arethe most preferred.

As discussed hereinbefore, all of the unsaturated materials that arerelated to the other preferred principal solvents herein by the samerelationship, i.e., having one more CH₂ group than the correspondingsaturated principal solvent and remaining within the effective ClogPrange are preferred. However, the specific preferred unsaturated diolprincipal solvents are: 1,3-butanediol, 2,2-diallyl-; 1,3-butanediol,2-(1-ethyl-1-propenyl)-; 1,3-butanediol, 2-(2-butenyl)-2-methyl-;1,3-butanediol, 2-(3-methyl-2-butenyl)-; 1,3-butanediol,2-ethyl-2-(2-propenyl)-; 1,3-butanediol,2-methyl-2-(1-methyl-2-propenyl)-; 1,4-butanediol,2,3-bis(1-methylethylidene)-; 1,3-pentanediol, 2-ethenyl-3-ethyl-;1,3-pentanediol, 2-ethenyl-4,4-dimethyl-; 1,4-pentanediol,3-methyl-2-(2-propenyl)-; 4-pentene-1,3-diol, 2-(1,1-dimethylethyl)-;4-pentene-1,3-diol, 2-ethyl-2,3-dimethyl-; 1,4-hexanediol,4-ethyl-2-methylene-; 1,5-hexadiene-3,4-diol, 2,3,5-trimethyl-;1,5-hexanediol, 2-(1-methylethenyl)-; 2-hexene-1,5-diol,4-ethenyl-2,5-dimethyl-; 1,4-heptanediol, 6-methyl-5-methylene-;2,4-heptadiene-2,6-diol, 4,6-dimethyl-; 2,6-heptadiene-1,4-diol,2,5,5-trimethyl-; 2-heptene-1,4-diol, 5,6-dimethyl-; 3-heptene-1,5-diol,4,6-dimethyl-; 5-heptene-1,3-diol, 2,4-dimethyl-; 5-heptene-1,3-diol,3,6-dimethyl-; 5-heptene-1,4-diol, 2,6-dimethyl-; 5-heptene-1,4-diol,3,6-dimethyl-; 6-heptene-1,3-diol, 2,2-dimethyl-; 6-heptene-1,4-diol,5,6-dimethyl-; 6-heptene-1,5-diol, 2,4-dimethyl-; 6-heptene-1,5-diol,2-ethylidene-6-methyl-; 6-heptene-2,4-diol, 4-(2-propenyl)-;1-octene-3,6-diol, 3-ethenyl-; 2,4,6-octatriene-1,8-diol, 2,7-dimethyl-;2,5-octadiene-1,7-diol, 2,6-dimethyl-; 2,5-octadiene-1,7-diol,3,7-dimethyl-; 2,6-octadiene-1,4-diol, 3,7-dimethyl-(Rosiridol);2,6-octadiene-1,8-diol, 2-methyl-; 2,7-octadiene-1,4-diol,3,7-dimethyl-; 2,7-octadiene-1,5-diol, 2,6-dimethyl-;2,7-octadiene-1,6-diol, 2,6-dimethyl-(8-hydroxylinalool);2,7-octadiene-1,6-diol, 2,7-dimethyl-; 2-octene-1,7-diol,2-methyl-6-methylene-; 3,5-octadiene-2,7-diol, 2,7-dimethyl-;3,5-octanediol, 4-methylene-; 3,7-octadiene-1,6-diol, 2,6-dimethyl-;4-octene-1,8-diol, 2-methylene-; 6-octene-3,5-diol, 2-methyl-;6-octene-3,5-diol, 4-methyl-; 7-octene-2,4-diol, 2-methyl-6-methylene-;7-octene-2,5-diol, 7-methyl-; 7-octene-3,5-diol, 2-methyl-;1-nonene-3,5-diol; 1-nonene-3,7-diol; 3-nonene-2,5-diol;4-nonene-2,8-diol; 6,8-nonadiene-1,5-diol; 7-nonene-2,4-diol;8-nonene-2,4-diol; 8-nonene-2,5-diol; 1,9-decadiene-3,8-diol; and/or1,9-decadiene-4,6-diol.

Said principal alcohol solvent can also preferably be selected from thegroup consisting of: 2,5-dimethyl-2,5-hexanediol;2-ethyl-1,3-hexanediol; 2-methyl-2-propyl-1,3-propanediol;1,2-hexanediol; and mixtures thereof. More preferably said principalalcohol solvent is selected from the group consisting of2-ethyl-1,3-hexanediol; 2-methyl-2-propyl-1,3-propanediol;1,2-hexanediol; and mixtures thereof. Even more preferably, saidprincipal alcohol solvent is selected from the groups consisting of2-ethyl-1,3-hexanediol; 1,2-hexanediol; and mixtures thereof.

When several derivatives of the same diol with different alkyleneoxygroups can be used, e.g., 2-methyl-2,3-butanediol having 3 to 5ethyleneoxy groups, or 2 propyleneoxy groups, or 1 butyleneoxy group, itis preferred to use the derivative with the lowest number of groups,i.e., in this case, the derivative with one butyleneoxy group. However,when only about one to about four ethyleneoxy groups are needed toprovide good formulatability, such derivatives are also preferred.

UNSATURATED DIOLS

It is found surprisingly that there is a clear similarity between theacceptability (formulatability) of a saturated diol and its unsaturatedhomologs, or analogs, having higher molecular weights. The unsaturatedhomologs/analogs have the same formlatability as the parent saturatedprincipal solvent with the condition that the unsaturated principalsolvents have one additional methylene (viz., CH₂) group for each doublebond in the chemical formula. In other words, there is an apparent“addition rule” in that. for each good saturated principal solvent ofthis invention, which is suitable for the formulation of clear,concentrated fabric softener compositions, there are suitableunsaturated principal solvents where one, or more, CH₂ groups are addedwhile, for each CH₂ group added, two hydrogen atoms are removed fromadjacent carbon atoms in the molecule to form one carbon—carbon doublebond, thus holding the number of hydrogen atoms in the molecule constantwith respect to the chemical formula of the “parent” saturated principalsolvent. This is due to a surprising fact that adding a —CH₂— group to asolvent chemical formula has an effect of increasing its ClogP value byabout 0.53, while removing two adjacent hydrogen atoms to form a doublebond has an effect of decreasing its ClogP value by about a similaramount, viz., about 0.48, thus about compensating for the —CH₂—addition. Therefore one goes from a preferred saturated principalsolvent to the preferred higher molecular weight unsaturatedanalogs/homologs containing at least one more carbon atom by insertingone double bond for each additional CH₂ group, and thus the total numberof hydrogen atoms is kept the same as in the parent saturated principalsolvent, as long as the ClogP value of the new solvent remains withinthe effective 0.15-0.64, preferably from about 0.25 to about 0.62, andmore preferably from about 0.40 to about 0.60, range. The following aresome illustrative examples:

2,2-Dimethyl-6-heptene-1,3-diol (CAS No. 140192-39-8) is a preferredC9-diol principal solvent and can be considered to be derived byappropriately adding a CH₂ group and a double bond to either of thefollowing preferred C8-diol principal solvents: 2-methyl-1,3-heptanediolor 2,2-dimethyl-1,3-hexanediol.

2,4-Dimethyl-5-heptene-1,3-diol (CAS No. 123363-69-9) is a preferredC9-diol principal solvent and can be considered to be derived byappropriately adding a CH₂ group and a double bond to either of thefollowing preferred C8-diol principal solvents: 2-methyl-1,3-heptanediolor 2,4-dimethyl-1,3-hexanediol.

2-(1-Ethyl-1-propenyl)-1,3-butanediol (CAS No. 116103-35-6) is apreferred C9-diol principal solvent and can be considered to be derivedby appropriately adding a CH₂ group and a double bond to either of thefollowing preferred C8-diol principal solvents:2-(1-ethylpropyl)-1,3-propanediol or 2-(1-methylpropyl)-1,3-butanediol.

2-Ethenyl-3-ethyl-1,3-pentanediol (CAS No. 104683-37-6) is a preferredC9-diol principal solvent and can be considered to be derived byappropriately adding a CH₂ group and a double bond to either of thefollowing preferred C8-diol principal solvents:3-ethyl-2-methyl-1,3-pentanediol or 2-ethyl-3-methyl-1,3-pentanediol.

3,6-Dimethyl-5-heptene-1,4-diol (e.g., CAS No. 106777-99-5) is apreferred C9-diol principal solvent and can be considered to be derivedby appropriately adding a CH₂ group and a double bond to any of thefollowing preferred C8-diol principal solvents:3-methyl-1,4-heptanediol; 6-methyl-1,4-heptanediol; or3,5-dimethyl-1,4-hexanediol.

5,6-Dimethyl-6-heptene-1,4-diol (e.g., CAS No. 152344-16-6) is apreferred C9-diol principal solvent and can be considered to be derivedby appropriately adding a CH₂ group and a double bond to any of thefollowing preferred C8-diol principal solvents:5-methyl-1,4-heptanediol; 6-methyl-1,4-heptanediol; or4,5-dimethyl-1,3-hexanediol.

4-Methyl-6-octene-3,5-diol (CAS No. 156414-25-4) is a preferred C9-diolprincipal solvent and can be considered to be derived by appropriatelyadding a CH₂ group and a double bond to any of the following preferredC8-diol principal solvents: 3,5-octanediol, 3-methyl-2,4-heptanediol or4-methyl-3,5-heptanediol.

Rosiridol (CAS No. 101391-01-9) and isorosiridol (CAS No. 149252-15-3)are two isomers of 3,7-dimethyl-2,6-octadiene-1,4-diol, and arepreferred C10-diol principal solvents. They can be considered to bederived by appropriately adding two CH₂ groups and two double bonds toany of the following preferred C8-diol principal solvents:2-methyl-1,3-heptanediol; 6-methyl-1,3-heptanediol;3-methyl-1,4-heptanediol; 6-methyl-1,4-heptanediol;2,5-dimethyl-1,3-hexanediol; or 3,5-dimethyl-1,4-hexanediol.

8-Hydroxylinalool (CAS No. 103619-06-3,2,6-dimethyl-2,7-octadiene-1,6-diol) is a preferred C10-diol principalsolvent and can be considered to be derived by appropriately adding twoCH₂ groups and two double bonds to any of the following preferredC8-diol principal solvents: 2-methyl-1,5-heptanediol;5-methyl-1,5-heptanediol; 2-methyl-1,6-heptanediol;6-methyl-1,6-heptanediol; or 2,4-dimethyl-1,4-hexanediol.

2,7-Dimethyl-3,7-octadiene-2,5-diol (CAS No. 171436-39-8) is a preferredC10-diol principal solvent and can be considered to be derived byappropriately adding two CH₂ group and two double bond to any of thefollowing preferred C8-diol principal solvents: 2,5-octanediol;6-methyl-1,4-heptanediol; 2-methyl-2,4-heptanediol;6-methyl-2,4-heptanediol; 2-methyl-2,5-heptanediol;6-methyl-2,5-heptanediol; and 2,5-dimethyl-2,4-hexanediol.

4-Butyl-2-butene-1,4-diol (CAS No. 153943-66-9) is a preferred C8-diolprincipal solvent and can be considered to be derived by appropriatelyadding a CH₂ group and a double bond to any of the following preferredC7-diol principal solvents: 2-propyl-1,4-butanediol or2-butyl-1,3-propanediol.

By the same token, there are cases where a higher molecular weightunsaturated homolog which is derived from a poor, inoperable saturatedsolvent is itself a poor solvent. For example,3,5-dimethyl-5-hexene-2,4-diol (e.g., CAS No. 160429-40-3) is a poorunsaturated C8 solvent, and can be considered to be derived from thefollowing poor saturated C7 solvents: 3-methyl-2,4-hexanediol;5-methyl-2,4-hexanediol; or 2,4-dimethyl-1,3-pentanediol; and2,6-dimethyl-5-heptene-1,2-diol (e.g., CAS No. 141505-71-7) is a poorunsaturated C9 solvent, and can be considered to be derived from thefollowing poor saturated C8 solvents: 2-methyl-1,2-heptanediol;6-methyl-1,2-heptanediol; or 2,5-dimethyl-1,2-hexanediol.

It is also found, surprisingly, that there is an exception to the aboveaddition rule, in which saturated principal solvents always haveunsaturated analogs/homologs with the same degree of acceptability. Theexception relates to saturated diol principal solvents having the twohydroxyl groups situated on two adjacent carbon atoms. In some cases,but not always, inserting one, or more, CH₂ groups between the twoadjacent hydroxyl groups of a poor solvent results in a higher molecularweight unsaturated homolog which is more suitable for the clear,concentrated fabric softener formulation. For example, the preferredunsaturated 6,6-dimethyl-1-heptene-3,5-diol (CAS No. 109788-01-4) havingno adjacent hydroxyl groups can be considered to be derived from theinoperable 2,2-dimethyl-3,4-hexanediol which has adjacent hydroxylgroups. In this case, it is more reliable to consider that the6,6-dimethyl-1-heptene-3,5-diol is derived from either2-methyl-3,5-heptanediol or 5,5-dimethyl-2,4-hexanediol which are bothpreferred principal solvents and do not have adjacent hydroxyl groups.Conversely, inserting CH₂ groups between the adjacent hydroxyl groups ofa preferred principal solvent can result in an inoperable highermolecular weight unsaturated diol solvent. For example, the inoperableunsaturated 2,4-dimethyl-5-hexene-2,4-diol (CAS No. 87604-24-8) havingno adjacent hydroxyl groups can be considered to be derived from thepreferred 2,3-dimethyl-2,3-pentanediol which has adjacent hydroxylgroups. In this case, it is more reliably to derive the inoperableunsaturated 2,4-dimethyl-5-hexene-2,4-diol from either2-methyl-2,4-hexanediol or 4-methyl-2,4-hexanediol which are bothinoperable solvents and do not have adjacent hydroxyl groups. There arealso cases where an inoperable unsaturated solvent having no adjacenthydroxyl groups can be considered to be derived from an inoperablesolvent which has adjacent hydroxyl groups, such as the pair4,5-dimethyl-6-hexene-1,3-diol and 3,4-dimethyl-1,2-pentanediol.Therefore, in order to deduce the formulatability of an unsaturatedsolvent having no adjacent hydroxyl groups, one should start from a lowmolecular weight saturated homolog also not having adjacent hydroxylgroups. I.e., in general, the relationship is more reliable when thedistance/relationship of the two hydroxy groups is maintained. I.e., itis reliable to start from a saturated solvent with adjacent hydroxylgroups to deduce the formulatability of the higher molecular weightunsaturated homologs also having adjacent hydroxyl groups.

It has been discovered that the use of these specific principal alcoholsolvents can produce clear, low viscosity, stable fabric softenercompositions at surprisingly low principal solvent levels, i.e., lessthan about 40%, by weight of the composition when the fabric softeneractives have the stated IVs and cis/trans ratios. It has also beendiscovered that the use of the principal alcohol solvents can producehighly concentrated fabric softener compositions, that are stable andcan be diluted, e.g. from about 2:1 to about 10:1, to producecompositions with lower levels of fabric softener that are still stable.

As previously discussed, the principal solvents are desirably kept tothe lowest levels that are feasible in the present compositions forobtaining translucency or clarity. The presence of water exerts animportant effect on the need for the principal solvents to achieveclarity of these compositions. The higher the water content, the higherthe principal solvent level (relative to the softener level) is neededto attain product clarity. Inversely, the less the water content, theless principal solvent (relative to the softener) is needed. Thus, atlow water levels of from about 5% to about 15%, the softeneractive-to-principal solvent weight ratio is preferably from about 55:45to about 85:15, more preferably from about 60:40 to about 80:20. Atwater levels of from about 15% to about 70%, the softeneractive-to-principal solvent weight ratio is preferably from about 45:55to about 70:30, more preferably from about 55:45 to about 70:30. But athigh water levels of from about 70% to about 80%, the softeneractive-to-principal solvent weight ratio is preferably from about 30:70to about 55:45, more preferably from about 35:65 to about 45:55. At evenhigher water levels, the softener to principal solvent ratios shouldalso be even higher.

Mixtures of the above principal solvents are particularly preferred,since one of the problems associated with large amounts of solvents issafety. Mixtures decrease the amount of any one material that ispresent. Odor and flammability can also be mimimized by use of mixtures,especially when one of the principal solvents is volatile and/or has anodor, which is more likely for low molecular weight materials. Suitablesolvents that can be used at levels that would not be sufficient toproduce a clear product are 2,2,4-trimethyl-1,3-pentane diol; theethoxylate, diethoxylate, or triethoxylate derivatives of2,2,4-trimethyl-1,3-pentane diol; and/or 2-ethyl-1,3-hexanediol. For thepurposes of this invention, these solvents should only be used at levelsthat will not provide a stable, or clear product. Preferred mixtures arethose where the majority of the solvent is one, or more, that have beenidentified hereinbefore as most preferred. The use of mixtures ofsolvents is also preferred, especially when one, or more, of thepreferred principal solvents are solid at room temperature. In thiscase, the mixtures are fluid, or have lower melting points, thusimproving processability of the softener compositions.

It is also discovered that it is possible to substitute for part of aprincipal solvent or a mixture of principal solvents of this inventionwith a secondary solvent, or a mixture of secondary solvents, which bythemselves are not operable as a principal solvent of this invention, aslong as an effective amount of the operable principal solvent(s) of thisinvention is still present in the liquid concentrated, clear fabricsoftener composition. An effective amount of the principal solvent(s) ofthis invention is at least greater than about 5%, preferably more thanabout 7%, more preferably more than about 10% of the composition, whenat least about 15% of the softener active is also present. Thesubstitute solvent(s) can be used at any level, but preferably aboutequal to, or less than, the amount of operable principal solvent, asdefined hereinbefore, that is present in the fabric softenercomposition.

For example, even though 1,2-pentanediol, 1,3-octanediol, and hydroxypivalyl hydroxy pivalate (hereinafter, HPHP) having the followingformula:

HO—CH₂—C(CH₃)₂—CH₂—O—CO—C(CH₃)₂CH₂—OH  (CAS # 1115-20-4)

are inoperable solvents according to this invention, mixtures of thesesolvents with the principal solvent, e.g., with the preferred1,2-hexanediol principal solvent, wherein the 1,2-hexanediol principalsolvent is present at effective levels, also provide liquidconcentrated, clear fabric softener compositions.

Some of the secondary solvents that can be used are those listed asinoperable hereinbefore and hereinafter, as well as some parent,non-alkoxylated solvents disclosed in Tables VIIIA-VIIIE.

The principal solvent can be used to either make a compositiontranslucent or clear, or can be used to reduce the temperature at whichthe composition is translucent or clear. Thus the invention alsocomprises the method of adding the principal solvent, at the previouslyindicated levels, to a composition that is not translucent, or clear, orwhich has a temperature where instability occurs that is too high, tomake the composition translucent or clear, or, when the composition isclear, e.g., at ambient temperature, or down to a specific temperature,to reduce the temperature at which instability occurs, preferably by atleast about 5° C., more preferably by at least about 10° C. Theprincipal advantage of the principal solvent is that it provides themaximum advantage for a given weight of solvent. It is understood that“solvent”, as used herein, refers to the effect of the principal solventand not to its physical formn at a given temperature, since some of theprincipal solvents are solids at ambient temperature.

Alkyl Lactates

Some alkyl lactate esters, e.g., ethyl lactate and isopropyl lactatehave ClogP values within the effective range of from about 0.15 to about0.64, and can form liquid concentrated, clear fabric softenercompositions with the fabric softener actives of this invention, butneed to be used at a slightly higher level than the more effective diolsolvents like 1,2-hexanediol. They can also be used to substitute forpart of other principal solvents of this invention to form liquidconcentrated, clear fabric softener compositions. This is illustrated inExample I-C.

III. OPTIONAL INGREDIENTS

(A) Low molecular weight water soluble solvents can also be used atlevels of of from 0% to about 12%, preferably from about 1% to about10%, more preferably from about 2% to about 8%. The water solublesolvents cannot provide a clear product at the same low levels of theprincipal solvents described hereinbefore but can provide clear productwhen the principal solvent is not sufficient to provide completely clearproduct. The presence of these water soluble solvents is thereforehighly desirable. Such solvents include: ethanol; isopropanol;1,2-propanediol; 1,3-propanediol; propylene carbonate; etc. but do notinclude any of the principal solvents (B). These water soluble solventshave a greater affinity for water in the presence of hydrophobicmaterials like the softener active than the principal solvents.

(B) Brighteners

The compositions herein can also optionally contain from about 0.005% to5% by weight of certain types of hydrophilic optical brighteners whichalso provide a dye transfer inhibition action. If used, the compositionsherein will preferably comprise from about 0.001% to 1% by weight ofsuch optical brighteners.

The hydrophilic optical brighteners useful in the present invention arethose having the structural formula:

wherein R₁ is selected from anilino, N-2-bis-hydroxyethyl andNH-2-hydroxyethyl; R₂ is selected from N-2-bis-hydroxyethyl,N-2-hydroxyethyl-N-methylamino, morphilino, chloro and amino; and M is asalt-forming cation such as sodium or potassium.

When in the above formula, R₁ is anilino, R₂ is N-2-bis-hydroxyethyl andM is a cation such as sodium, the brightener is4,4′,-bis[(4-anilino-6-(N-2-bis-hydroxyethyl)-s-triazine-2-yl)amino]-2,2′-stilbenedisulfonicacid and disodium salt. This particular brightener species iscommercially marketed under the tradename Tinopal-UNPA-GX® by Ciba-GeigyCorporation. Tinopal-UNPA-GX is the preferred hydrophilic opticalbrightener useful in the rinse added compositions herein.

When in the above formula, R₁ is anilino, R₂ isN-2-hydroxyethyl-N-2-methylamino and M is a cation such as sodium, thebrightener is4,4′-bis[(4-anilino-6-(N-2-hydroxyethyl-N-methylamino)-s-triazine-2-yl)amino]2,2′-stilbenedisulfonicacid disodium salt. This particular brightener species is commerciallymarketed under the tradename Tinopal 5BM-GX® by Ciba-Geigy Corporation.

When in the above formula, R₁ is anilino, R₂ is morphilino and M is acation such as sodium, the brightener is4,4′-bis[(4-anilino-6-morphilino-s-triazine-2-yl)amino]2,2′-stilbenedisulfonicacid, sodium salt. This particular brightener species is commerciallymarketed under the tradename Tinopal AMS-GX® by Ciba Geigy Corporation.

(C) Optional Viscosity/Dispersibility Modifiers

Relatively concentrated compositions containing both saturated andunsaturated diester quaternary ammonium compounds can be prepared thatare stable without the addition of concentration aids. However, thecompositions of the present invention may require organic and/orinorganic concentration aids to go to even higher concentrations and/orto meet higher stability standards depending on the other ingredients.These concentration aids which typically can be viscosity modifiers maybe needed, or preferred, for ensuring stability under extreme conditionswhen particular softener active levels are used. The surfactantconcentration aids are typically selected from the group consisting of(1) single long chain alkyl cationic surfactants; (2) nonionicsurfactants; (3) amine oxides; (4) fatty acids; and (5) mixturesthereof. These aids are described in P&G Copending application Ser. No.08/461,207, filed Jun. 5, 1995, Wahl et al., specifically on page 14,line 12 to page 20, line 12, which is herein incorporated by reference.

When said dispersibility aids are present, the total level is from about2% to about 25%, preferably from about 3% to about 17%, more preferablyfrom about 4% to about 15%, and even more preferably from 5% to about13% by weight of the composition. These materials can either be added aspart of the active softener raw material, (I), e.g., the mono-long chainalkyl cationic surfactant and/or the fatty acid which are reactants usedto form the biodegradable fabric softener active as discussedhereinbefore, or added as a separate component. The total level ofdispersibility aid includes any amount that may be present as part ofcomponent (I).

(1) Mono-Alkyl Cationic Quaternary Ammonium Compound

When the mono-alkyl cationic quaternary ammonium compound is present, itis typically present at a level of from about 2% to about 25%,preferably from about 3% to about 17%, more preferably from about 4% toabout 15%, and even more preferably from 5% to about 13% by weight ofthe composition, the total mono-alkyl cationic quaternary ammoniumcompound being at least at an effective level.

Such mono-alkyl cationic quaternary ammonium compounds useful in thepresent invention are, preferably, quaternary ammonium salts of thegeneral formula:

[R⁴N⁺(R⁵)₃]A⁻

wherein

R⁴ is C₈-C₂₂ alkyl or alkenyl group, preferably C₁₀-C₁₈ alkyl or alkenylgroup;

more preferably C₁₀-C₁₄ or C₁₆-C₁₈ alkyl or alkenyl group;

each R⁵ is a C₁-C₆ alkyl or substituted alkyl group (e.g., hydroxyalkyl), preferably C₁-C₃ alkyl group, e.g., methyl (most preferred),ethyl, propyl, and the like, a benzyl group, hydrogen, a polyethoxylatedchain with from about 2 to about 20 oxyethylene units, preferably fromabout 2.5 to about 13 oxyethylene units, more preferably from about 3 toabout 10 oxyethylene units, and mixtures thereof, and

A⁻ is as defined hereinbefore for (Formula (I)).

Especially preferred dispersibility aids are monolauryl trimethylammonium chloride and monotallow trimethyl ammonium chloride availablefrom Witco under the trade name Varisoft® 471 and monooleyl trimethylammonium chloride available from Witco under the tradename Varisoft®417.

The R⁴ group can also be attached to the cationic nitrogen atom througha group containing one, or more, ester, amide, ether, amine, etc.,linking groups which can be desirable for increased concentratability ofcomponent (I), etc. Such linking groups are preferably within from aboutone to about three carbon atoms of the nitrogen atom.

Mono-alkyl cationic quaternary ammonium compounds also include C₈-C₂₂alkyl choline esters. The preferred dispersibility aids of this typehave the formula:

R¹C(O)—O—CH₂CH₂N⁺(R)₃A⁻

wherein R¹, R and A⁻ are as defined previously.

Highly preferred dispersibility aids include C₁₂-C₁₄ coco choline esterand C₁₆-C₁₈ tallow choline ester.

Suitable biodegradable single-long-chain alkyl dispersibility aidscontaining an ester linkage in the long chains are described in U.S.Pat. No. 4,840,738, Hardy and Walley, issued Jun. 20, 1989, said patentbeing incorporated herein by reference.

When the dispersibility aid comprises alkyl choline esters, preferablythe compositions also contain a small amount, preferably from about 2%to about 5% by weight of the composition, of organic acid. Organic acidsare described in European Patent Application No. 404,471, Machin et al.,published on Dec. 27, 1990, supra, which is herein incorporated byreference. Preferably the organic acid is selected from the groupconsisting of glycolic acid, acetic acid, citric acid, and mixturesthereof.

Ethoxylated quaternary ammonium compounds which can serve as thedispersibility aid include ethylbis(polyethoxy ethanol)alkylammoniumethyl-sulfate with 17 moles of ethylene oxide, available under the tradename Variquat® 66 from Sherex Chemical Company; polyethylene glycol (15)oleammonium chloride, available under the trade name Ethoquad® 0/25 fromAkzo; and polyethylene glycol (15) cocomonium chloride, available underthe trade name Ethoquad® C/25 from Akzo.

Suitable mono-long chain materials correspond to the softener activesdisclosed above, where only one R¹ group is present in the molecule. TheR¹ group or YR¹ group, is replaced normally by an R group.

Although the main function of the dispersibility aid is to increase thedispersibility of the ester softener, preferably the dispersibility aidsof the present invention also have some softening properties to boostsoftening performance of the composition. Therefore, preferably thecompositions of the present invention are essentially free ofnon-nitrogenous ethoxylated nonionic dispersibility aids which willdecrease the overall softening performance of the compositions.

Also, quaternary compounds having only a single long alkyl chain, canprotect the cationic softener from interacting with anionic surfactantsand/or detergent builders that are carried over into the rinse from thewash solution. It is highly desirable to have sufficient single longchain quaternary compound, or cationic polymer to tie up the anionicsurfactant. This provides improved wrinkle control. The ratio of fabricsoftener active to single long chain compound is Itypically from about100:1 to about 2:1, preferably from about 50:1 to about 5:1, morepreferably from about 13:1 to about 8:1. Under high detergent carry-overconditions, the ratio is preferably from about 5:1 to about 7:1.Typically the single long chain compound is present at a level of about10 ppm to about 25 ppm in the rinse.

(2) Amine Oxides

Suitable amine oxides include those with one alkyl or hydroxyalkylmoiety of about 8 to about 22 carbon atoms, preferably from about 10 toabout 18 carbon atoms, more preferably from about 8 to about 14 carbonatoms, and two alkyl moieties selected from the group consisting ofalkyl groups and hydroxyalkyl groups with about 1 to about 3 carbonatoms.

Examples include dimethyloctylamine oxide, diethyldecylamine oxide,bis-(2-hydroxyethyl)dodecyl-amine oxide, dimethyldodecylamine oxide,dipropyltetradecylamine oxide, methylethylhexadecylamine oxide,dimethyl-2-hydroxyoctadecylamine oxide, and coconut fatty alkyldimethylamine oxide.

(D) Stabilizers

Stabilizers can be present in the compositions of the present invention.The term “stabilizer,” as used herein, includes antioxidants andreductive agents. These agents are present at a level of from 0% toabout 2%, preferably from about 0.01% to about 0.2%, more preferablyfrom about 0.035% to about 0.1% for antioxidants, and, preferably, fromabout 0.01% to about 0.2% for reductive agents. These assure good odorstability under long term storage conditions. Antioxidants and reductiveagent stabilizers are especially critical for unscented or low scentproducts (no or low perfume).

Examples of antioxidants that can be added to the compositions of thisinvention include a mixture of ascorbic acid, ascorbic palmitate, propylgallate, available from Eastman Chemical Products, Inc., under the tradenames Tenox® PG and Tenox® S-1; a mixture of BHT (butylatedhydroxytoluene), BHA (butylated hydroxyanisole), propyl gallate, andcitric acid, available from Eastman Chemical Products, Inc., under thetrade name Tenox®-6; butylated hydroxytoluene, available from UOPProcess Division under the trade name Sustane® BHT; tertiarybutylhydroquinone, Eastman Chemical Products, Inc., as Tenox® TBHQ;natural tocopherols, Eastman Chemical Products, Inc., as Tenox®GT-1/GT-2; and butylated hydroxyanisole, Eastman Chemical Products,Inc., as BHA; long chain esters (C₈-C₂₂) of gallic acid, e.g., dodecylgallate; Irganox® 1010; Irganox® 1035; Irganox® B 1171; Irganox® 1425;Irganox® 3114; Irganox® 3125; and mixtures thereof; preferably Irganox®3125, Irganox® 1425, Irganox® 3114, and mixtures thereof; morepreferably Irganox® 3125 alone or mixed with citric acid and/or otherchelators such as isopropyl citrate, Dequest® 2010, available fromMonsanto with a chemical name of 1-hydroxyethylidene-1,1-diphosphonicacid (etidronic acid), and Tiron®, available from Kodak with a chemicalname of 4,5-dihydroxy-m-benzene-sulfonic acid/sodium salt, and DTPAV,available from Aldrich with a chemical name ofdiethylenetriaminepentaacetic acid.

(E) Soil Release Agent

In the present invention, an optional soil release agent can be added.The addition of the soil release agent can occur in combination with thepremix, in combination with the acid/water seat, before or afterelectrolyte addition, or after the final composition is made. Thesoftening composition prepared by the process of the present inventionherein can contain from 0% to about 10%, preferably from 0.2% to about5%, of a soil release agent. Preferably, such a soil release agent is apolymer. Polymeric soil release agents useful in the present inventioninclude copolymeric blocks of terephthalate and polyethylene oxide orpolypropylene oxide, and the like.

A preferred soil release agent is a copolymer having blocks ofterephthalate and polyethylene oxide. More specifically, these polymersare comprised of repeating units of ethylene terephthalate andpolyethylene oxide terephthalate at a molar ratio of ethyleneterephthalate units to polyethylene oxide terephthalate units of from25:75 to about 35:65, said polyethylene oxide terephthalate containingpolyethylene oxide blocks having molecular weights of from about 300 toabout 2000. The molecular weight of this polymeric soil release agent isin the range of from about 5,000 to about 55,000.

Another preferred polymeric soil release agent is a crystallizablepolyester with repeat units of ethylene terephthalate units containingfrom about 10% to about 15% by weight of ethylene terephthalate unitstogether with from about 10% to about 50% by weight of polyoxyethyleneterephthalate units, derived from a polyoxyethylene glycol of averagemolecular weight of from about 300 to about 6,000, and the molar ratioof ethylene terephthalate units to polyoxyethylene terephthalate unitsin the crystallizable polymeric compound is between 2:1 and 6:1.Examples of this polymer include the commercially available materialsZelcon 4780® (from Dupont) and Milease T® (from ICI).

Highly preferred soil release agents are polymers of the genericformula:

in which each X can be a suitable capping group, with each X typicallybeing selected from the group consisting of H, and alkyl or acyl groupscontaining from about 1 to about 4 carbon atoms. p is selected for watersolubility and generally is from about 6 to about 113, preferably fromabout 20 to about 50. u is critical to formulation in a liquidcomposition having a relatively high ionic strength. There should bevery little material in which u is greater than 10. Furthermore, thereshould be at least 20%, preferably at least 40%, of material in which uranges from about 3 to about 5.

The R¹⁴ moieties are essentially 1,4-phenylene moieties. As used herein,the term “the R¹⁴ moieties are essentially 1,4-phenylene moieties”refers to compounds where the R¹⁴ moieties consist entirely of1,4-phenylene moieties, or are partially substituted with other aryleneor alkarylene moieties, alkenyl moieties, alkenylene moieties, ormixtures thereof. Arylene and alkarylene moieties which can be partiallysubstituted for 1,4-phenylene include 1,3-phenylene, 1,2-phenylene,1,8-naphthylene, 1,4-naphthylene, 2,2-biphenylene, 4,4-biphenylene, andmixtures thereof. Alkylene and alkenylene moieties which can bepartially substituted include 1,2-propylene, 1,4-butylene,1,5-pentylene, 1,6-hexamethylene, 1,7-heptamethylene, 1,8-octamethylene,1,4-cyclohexylene, and mixtures thereof.

For the R¹⁴ moieties, the degree of partial substitution with moietiesother than 1,4-phenylene should be such that the soil release propertiesof the compound are not adversely affected to any great extent.Generally the degree of partial substitution which can be tolerated willdepend upon the backbone length of the compound, i.e., longer backbonescan have greater partial substitution for 1,4-phenylene moieties.Usually, compounds where the R¹⁴ comprise from about 50% to about 100%1,4-phenylene moieties (from 0% to about 50% moieties other than1,4-phenylene) have adequate soil release activity. For example,polyesters made according to the present invention with a 40:60 moleratio of isophthalic (1,3-phenylene) to terephthalic (1,4-phenylene)acid have adequate soil release activity. However, because mostpolyesters used in fiber making comprise ethylene terephthalate units,it is usually desirable to minimize the degree of partial substitutionwith moieties other than 1,4-phenylene for best soil release activity.Preferably, the R¹⁴ moieties consist entirely of (i.e., comprise 100%)1,4-phenylene moieties, i.e., each R¹⁴ moiety is 1,4-phenylene.

For the R¹⁵ moieties, suitable ethylene or substituted ethylene moietiesinclude ethylene, 1,2-propylene, 1,2-butylene, 1,2-hexylene,3-methoxy-1,2-propylene, and mixtures thereof. Preferably, the R¹⁵moieties are essentially ethylene moieties, 1,2 propylene moieties, ormixtures thereof. Inclusion of a greater percentage of ethylene moietiestends to improve the soil release activity of compounds. Surprisingly,inclusion of a greater percentage of 1,2-propylene moieties tends toimprove the water solubility of compounds.

Therefore, the use of 1,2-propylene moieties or a similar branchedequivalent is desirable for incorporation of any substantial part of thesoil release component in the liquid fabric softener compositions.Preferably, from about 75% to about 100%, are 1,2-propylene moieties.

The value for each p is at least about 6, and preferably is at leastabout 10. The value for each n usually ranges from about 12 to about113. Typically the value for each p is in the range of from about 12 toabout 43.

A more complete disclosure of soil release agents is contained in U.S.Pat. No.: 4,661,267, Decker, Konig, Straathof, and Gosselink, issuedApr. 28, 1987; U.S. Pat. No. 4,711,730, Gosselink and Diehl, issued Dec.8, 1987; U.S. Pat. No. 4,749,596, Evans, Huntington, Stewart, Wolf, andZimmerer, issued Jun. 7, 1988; U.S. Pat. No. 4,818,569, Trinh,Gosselink, and Rattinger, issued Apr. 4, 1989; U.S. Pat. No. 4,877,896,Maldonado, Trinh, and Gosselink, issued Oct. 31, 1989; U.S. Pat. No.4,956,447, Gosselink et al., issues Sep. 11, 1990; and U.S. Pat. No.4,976,879, Maldonado, Trinh, and Gosselink, issued Dec. 11, 1990, all ofsaid patents being incorporated herein by reference.

These soil release agents can also act as scum dispersants.

(F) Scum Dispersant

In the present invention, the premix can be combined with an optionalscum dispersant, other than the soil release agent, and heated to atemperature at or above the melting point(s) of the components.

The preferred scum dispersants herein are formed by highly ethoxylatinghydrophobic materials. The hydrophobic material can be a fatty alcohol,fatty acid, fatty amine, fatty acid amide, amine oxide, quaternaryammonium compound, or the hydrophobic moieties used to form soil releasepolymers. The preferred scum dispersants are highly ethoxylated, e.g.,more than about 17, preferably more than about 25, more preferably morethan about 40, moles of ethylene oxide per molecule on the average, withthe polyethylene oxide portion being from about 76% to about 97%,preferably from about 81% to about 94%, of the total molecular weight.

The level of scum dispersant is sufficient to keep the scum at anacceptable, preferably unnoticeable to the consumer, level under theconditions of use, but not enough to adversely affect softening. Forsome purposes it is desirable that the scum is nonexistent. Depending onthe amount of anionic or nonionic detergent, etc., used in the washcycle of a typical laundering process, the efficiency of the rinsingsteps prior to the introduction of the compositions herein, and thewater hardness, the amount of anionic or nonionic detergent surfactantand detergency builder (especially phosphates and zeolites) entrapped inthe fabric (laundry) will vary. Normally, the minimum amount of scumdispersant should be used to avoid adversely affecting softeningproperties. Typically scum dispersion requiresat least about 2%,preferably at least about 4% (at least 6% and preferably at least 10%for maximum scum avoidance) based upon the level of softener active.However, at levels of about 10% (relative to the softener material) ormore, one risks loss of softening efficacy of the product especiallywhen the fabrics contain high proportions of nonionic surfactant whichhas been absorbed during the washing operation.

Preferred scum dispersants are: Brij 700®; Varonic U-250®; GenapolT-500®, Genapol T-800®; Plurafac A-79®; and Neodol 25-50®.

(G) Bactericides

Examples of bactericides used in the compositions of this inventioninclude glutaraldehyde, formaldehyde, 2-bromo-2-nitro-propane-1,3-diolsold by Inolex Chemicals, located in Philadelphia, Pa., under the tradename Bronopol®, and a mixture of 5-chloro-2-methyl-4-isothiazoline-3-oneand 2-methyl-4-isothiazoline-3-one sold by Rohm and Haas Company underthe trade name Kathon about 1 to about 1,000 ppm by weight of the agent.

(H) Perfume

The present invention can contain any softener compatible perfume.Suitable perfumes are disclosed in U.S. Pat. No. 5,500,138, Bacon etal., issued Mar. 19, 1996, said patent being incorporated herein byreference.

As used herein, perftune includes fragrant substance or mixture ofsubstances including natural (i.e., obtained by extraction of flowers,herbs, leaves, roots, barks, wood, blossoms or plants), artificial(i.e., a mixture of different nature oils or oil constituents) andsynthetic (i.e., synthetically produced) odoriferous substances. Suchmaterials are often accompanied by auxiliary materials, such asfixatives, extenders, stabilizers and solvents. These auxiliaries arealso included within the meaning of “perfume”, as used herein.Typically, perfumes are complex mixtures of a plurality of organiccompounds.

Examples of perfume ingredients useful in the perfumes of the presentinvention compositions include, but are not limited to, hexyl cinnamicaldehyde; amyl cinnamic aldehyde; amyl salicylate; hexyl salicylate;terpineol; 3,7-dimethyl-cis-2,6-octadien-1-ol; 2,6-dimethyl-2-octanol;2,6-dimethyl-7-octen-2-ol; 3,7-dimethyl-3-octanol;3,7-dimethyl-trans-2,6-octadien-1-ol; 3,7-dimethyl-6-octen-1-ol;3,7-dimethyl-1-octanol;2-methyl-3-(para-tert-butylphenyl)-propionaldehyde;4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde;tricyclodecenyl propionate; tricyclodecenyl acetate; anisaldehyde;2-methyl-2-(para-iso-propylphenyl)-propionaldehyde;ethyl-3-methyl-3-phenyl glycidate; 4-(para-hydroxyphenyl)-butan-2-one;1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one;para-methoxyacetophenone; para-methoxy-alpha-phenylpropene;methyl-2-n-hexyl-3-oxo-cyclopentane carboxylate; undecalactone gamma.

Additional examples of fragrance materials include, but are not limitedto, orange oil; lemon oil; grapefruit oil; bergamot oil; clove oil;dodecalactone gamma; methyl-2-(2-pentyl-3-oxo-cyclopentyl) acetate;beta-naphthol methylether; methyl-beta-naphthylketone; coumarin;decylaldehyde; benzaldehyde; 4-tert-butylcyclohexyl acetate;alpha,alpha-dimethylphenethyl acetate; methylphenylcarbinyl acetate;Schiffs base of4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde and methylanthranilate; cyclic ethyleneglycol diester of tridecandioic acid;3,7-dimethyl-2,6-octadiene-1-nitrile; ionone gamma methyl; ionone alpha;ionone beta; petitgrain; methyl cedrylone;7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetranethyl-naphthalene;ionone methyl; methyl-1,6,10-trimethyl-2,5,9-cyclododecatrien-1-ylketone; 7-acetyl-1,1,3,4,4,6-hexamethyl tetralin;4-acetyl-6-tert-butyl-1,1-dimethyl indane; benzophenone;6-acetyl-1,1,2,3,3,5-hexamethyl indane;5-acetyl-3-isopropyl-1,1,2,6-tetramethyl indane; 1-dodecanal;7-hydroxy-3,7-dimethyl octanal; 10-undecen-1-al; iso-hexenyl cyclohexylcarboxaldehyde; formyl tricyclodecan; cyclopentadecanolide;16-hydroxy-9-hexadecenoic acid lactone;1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyicyclopenta-gamma-2-benzopyrane;ambroxane; dodecahydro-3a,6,6,9a-tetramethylnaphtho-[2,1b]furan; cedrol;5-(2,2,3-trimethylcyclopent-3-enyl)-3-methylpentan-2-ol;2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol;caryophyllene alcohol; cedryl acetate; para-tert-butylcyclohexylacetate; patchouli; olibanum resinoid; labdanum; vetivert; copaibabalsam; fir balsam; and condensation products of: hydroxycitronellal andmethyl anthranilate; hydroxycitronellal and indol; phenyl acetaldehydeand indol; 4-(4-hydroxy4-methyl pentyl)-3-cyclohexene-1-carboxaldehydeand methyl anthranilate.

More examples of perfume components are geraniol; geranyl acetate;linalool; linalyl acetate; tetrahydrolinalool; citronellol; citronellylacetate; dihydromyrcenol; dihydromyrcenyl acetate; tetrahydromyrcenol;terpinyl acetate; nopol; nopyl acetate; 2-phenylethanol; 2-phenylethylacetate; benzyl alcohol; benzyl acetate; benzyl salicylate; benzylbenzoate; styrallyl acetate; dimethylbenzylcarbinol;trichloromethylphenylcarbinyl methylphenylcarbinyl acetate; isononylacetate; vetiveryl acetate; vetiverol;2-methyl-3-(p-tert-butylphenyl)-propanal;2-methyl-3-(p-isopropylphenyl)-propanal;3-(p-tert-butylphenyl)-propanal;4-(4-methyl-3-pentenyl)-3-cyclohexenecarbaldehyde;4-acetoxy-3-pentyltetrahydropyran; methyl dihydrojasmonate;2-n-heptylcyclopentanone; 3-methyl-2-pentyl-cyclopentanone; n-decanal;n-dodecanal; 9-decenol-1; phenoxyethyl isobutyrate; phenylacetaldehydedimethylacetal; phenylacetaldehyde diethylacetal; geranonitrile;citronellonitrile; cedryl acetal; 3-isocamphylcyclohexanol; cedrylmethylether; isolongifolanone; aubepine nitrile; aubepine; heliotropine;eugenol; vanillin; diphenyl oxide; hydroxycitronellal ionones; methylionones; isomethyl ionomes; irones; cis-3-hexenol and esters thereof;indane musk fragrances; tetralin musk fragrances; isochroman muskfragrances; macrocyclic ketones; macrolactone musk fragrances; ethylenebrassylate.

The perfumes useful in the present invention compositions aresubstantially free of halogenated materials and nitromusks.

Suitable solvents, diluents or carriers for perfirmes ingredientsmentioned above are for examples, ethanol, isopropanol, diethyleneglycol, monoethyl ether, dipropylene glycol, diethyl phthalate, triethylcitrate, etc. The amount of such solvents, diluents or carriersincorporated in the perfumes is preferably kept to the minimum needed toprovide a homogeneous perfume solution.

Perfume can be present at a level of from 0% to about 15%, preferablyfrom about 0.1% to about 8%, and more preferably from about 0.2% toabout 5%, by weight of the finished composition. Fabric softenercompositions of the present invention provide improved fabric perfumedeposition.

(I) Chelating Agents

The compositions and processes herein can optionally employ one or morecopper and/or nickel chelating agents (“chelators”). Such water-solublechelating agents can be selected from the group consisting of aminocarboxylates, amino phosphonates, polyfumctionally-substituted aromaticchelating agents and mixtures thereof, all as hereinafter defined. Thewhiteness and/or brightness of fabrics are substantially improved orrestored by such chelating agents and the stability of the materials inthe compositions are improved.

Amino carboxylates useful as chelating agents herein includeethylenedi-arninetetraacetates (EDTA),N-hydroxyethylethylenediarninetriacetates, nitrilotri-acetates (NTA),ethylenediamine tetraproprionates, ethylenediamine-N,N′-diglutamates,2-hyroxypropylenediamine-N,N′-disuccinates,triethylenetetraaminehexacetates, diethylenetriaminepentaacetates(DETPA), and ethanoldiglycines, including their water-soluble salts suchas the alkali metal, amnmonium, and substituted ammonium salts thereofand mixtures thereof.

Amino phosphonates are also suitable for use as chelating agents in thecompositions of the invention when at least low levels of totalphosphorus are permitted in detergent compositions, and includeethylenediaminetetrakis (methylenephosphonates),diethylenetriamine-N,N,N′,N″,N″-pentakis(methane phosphonate) (DETMP)and 1-hydroxyethane-1,1-diphosphonate (HEDP). Preferably, these aminophosphonates to not contain alkyl or alkenyl groups with more than about6 carbon atoms.

The chelating agents are typically used in the present rinse process atlevels from about 2 ppm to about 25 ppm, for periods from 1 minute up toseveral hours' soaking.

The preferred EDDS chelator used herein (also known asethylenediamine-N,N′-disuccinate) is the material described in U.S. Pat.No. 4,704,233, cited hereinabove, and has the formula (shown in freeacid form):

HN(L)C₂H₄N(L)H

wherein L is a CH₂(COOH)CH₂(COOH) group.

As disclosed in the patent, EDDS can be prepared using maleic anhydrideand ethylenediamine. The preferred biodegradable [S,S] isomer of EDDScan be prepared by reacting L-aspartic acid with 1,2-dibromoethane. TheEDDS has advantages over other chelators in that it is effective forchelating both copper and nickel cations, is available in abiodegradable form, and does not contain phosphorus. The EDDS employedherein as a chelator is typically in its salt form, i.e., wherein one ormore of the four acidic hydrogens are replaced by a water-soluble cationM, such as sodium, potassium, ammonium, triethanolammonium, and thelike. As noted before, the EDDS chelator is also typically used in thepresent rinse process at levels from about 2 ppm to about 25 ppm forperiods from 1 minute up to several hours' soaking. At certain pH's theEDDS is preferably used in combination with zinc cations.

A wide variety of chelators can be used herein. Indeed, simplepolycarboxylates such as citrate, oxydisuccinate, and the like, can alsobe used, although such chelators are not as effective as the aminocarboxylates and phosphonates, on a weight basis. Accordingly, usagelevels may be adjusted to take into account differing degrees ofchelating effectiveness. The chelators herein will preferably have astability constant (of the fully ionized chelator) for copper ions of atleast about 5, preferably at least about 7. Typically, the chelatorswill comprise from about 0.5% to about 10%, more preferably from about0.75% to about 5%, by weight of the compositions herein, in addition tothose that are stabilizers. Preferred chelators include DETMP, DETPA,NTA, EDDS and mixtures thereof.

(J) Cationic Polymers

Composition herein can contain from about 0.001% to about 10%,preferably from about 0.01% to about 5%, more preferably from about 0.1%to about 2%, of cationic polymer, typically having a molecular weight offrom about 500 to about 1,000,000, preferably from about 1,000 to about500,000, more preferably from about 1,000 to about 250,000, and evenmore preferably from about 2,000 to about 100,000 and a charge densityof at least about 0.01 meq/gm., preferably from about 0.1 to about 8meq/gm., more preferably from about 0.5 to about 7, and even morepreferably from about 2 to about 6. In order to provide the benefits ofthe cationic polymers, and especially cationic polymers containingamine, or imine, groups, said cationic polymer is preferably primarilyin the continuous aqueous phase.

The cationic polymers of the present invention can be amine salts orquaternary ammonium salts. Preferred are quaternary ammonium salts. Theyinclude cationic derivatives of natural polymers such as somepolysaccharide, gums, starch and certain cationic synthetic polymerssuch as polymers and co-polymers of cationic vinyl pyridine or vinylpyridinium halides. Preferably the polymers are water soluble, forinstance to the extent of at least 0.5% by weight at 20° C. Preferablythey have molecular weights of from about 600 to about 1,000,000, morepreferably from about 600 to about 500,000, even more preferably fromabout 800 to about 300,000, and especially from about 1000 to 10,000. Asa general rule, the lower the molecular weight the higher the degree ofsubstitution (D.S.) by cationic, usually quaternary groups, which isdesirable, or, correspondingly, the lower the degree of substitution thehigher the molecular weight which is desirable, but no preciserelationship appears to exist. In general, the cationic polymers shouldhave a charge density of at least about 0.01 meq/gm., preferably fromabout 0.1 to about 8 meq/gm., more preferably from about 0.5 to about 7,and even more preferably from about 2 to about 6.

Suitable desirable cationic polymers are disclosed in “CTFAInternational Cosmetic Ingredient Dictionary, Fourth Edition, J. M.Nikitakis, et al, Editors, published by the Cosmetic, Toiletry, andFragrance Association, 1991, incorporated herein by reference. The listincludes the following:

Of the polysaccharide gums, guar and locust bean gums, which aregalactomannam gums are available commercially, and are preferred. Thusguar gums are marketed under Trade Names CSAA M/200, CSA 200/50 byMeyhall and Stein-Hall, and hydroxyalkylated guar gums are availablefrom the same suppliers. Other polysaccharide gums commerciallyavailable include: Xanthan Gum; Ghatti Gum; Tamarind Gum; Gum Arabic;and Agar.

Cationic guar gums and methods for making them are disclosed in BritishPat. No. 1,136,842 and U.S. Pat. No. 4,031,307. Preferably they have aD.S. of from 0.1 to about 0.5.

An effective cationic guar gum is Jaguar C-13S (Trade Name—Meyhall).Cationic guar gums are a highly preferred group of cationic polymers incompositions according to the invention and act both as scavengers forresidual anionic surfactant and also add to the softening effect ofcationic textile softeners even when used in baths containing little orno residual anionic surfactant. The other polysaccharide-based gums canbe quaternized similarly and act substantially in the same way withvarying degrees of effectiveness. Suitable starches and derivatives arethe natural starches such as those obtained from maize, wheat, barleyetc., and from roots such as potato, tapioca etc., and dextrins,particularly the pyrodextrins such as British gum and white dextrin.

Some very effective individual cationic polymers are the following:Polyvinyl pyridine, molecular weight about 40,000, with about 60% of theavailable pyridine nitrogens quatemized.; Co-polymer of 70/30 molarproportions of vinyl pyridine/styrene, molecular weight about 43,000,with about 45% of the available pyridine nitrogens quatemized as above.;Co-polymers of 60/40 molar proportions of vinyl pyridine/acrylamide,with about 35% of the available pyridine nitrogens quaternized as above.Co-polymers of 77/23 and 57/43 molar proportions of vinylpyridine/methyl methacrylate, molecular weight about 43,000, with about97% of the available pyridine nitrogens quaternized as above.

These cationic polymers are effective in the compositions at very lowconcentrations for instance from 0.001% by weight to 0.2% especiallyfrom about 0.02% to 0.1%. In some instances the effectiveness seems tofall off, when the content exceeds some optimum level, such as forpolyvinyl pyridine and its styrene co-polymer about 0.05%.

Some other effective cationic polymers are: Co-polymer of vinyl pyridineand N-vinyl pyrrolidone (63/37) with about 40% of the available pyridinenitrogens quaternized.; Co-polymer of vinyl pyridine and acrylonitrile(60/40), quaternized as above.; Co-polymer of N,N-dimethyl amino ethylmethacrylate and styrene (55/45) quaternized as above at about 75% ofthe available amino nitrogens. Eudragit E (Trade Name of Rohm GmbH)quaternized as above at about 75% of the available amino nitrogens.Eudragit E is believed to be co-polymer of N,N-dialkyl amino alkylmethacrylate and a neutral acrylic acid ester, and to have molecularweight about 100,000 to 1,000,000. ; Co-polymer of N-vinyl pyrrolidoneand N,N-diethyl amino methyl methacrylate (40/50), quaternized at about50% of the available amino nitrogens.; These cationic polymers can beprepared in a known manner by quaternising the basic polymers.

Yet other cationic polymeric salts are quaternized polyethyleneimines.These have at least 10 repeating units, some or all being quaternized.Commercial examples of polymers of this class are also sold under thegeneric Trade Name Alcostat by Allied Colloids.

Typical examples of polymers are disclosed in U.S. Pat. No. 4,179,382,incorporated herein by reference.

Each polyamine nitrogen whether primary, secondary or tertiary, isfurther defined as being a member of one of three general classes;simple substituted, quaternized or oxidized.

The polymers are made neutral by water soluble anions such as chlorine(Cl⁻), bromine (Br⁻), iodine (I⁻) or any other negatively chargedradical such as sulfate (SO₄ ²⁻) and methosulfate (CH₃SO₃ ⁻).

Specific polyamine backbones are disclosed in U.S. Pat. No. 2,182,306,Ulrich et al., issued Dec. 5, 1939; U.S. Pat. No. 3,033,746, Mayle etal., issued May 8, 1962; U.S. Pat. No. 2,208,095, Esselmann et al.,issued Jul. 16, 1940; U.S. Pat. No. 2,806,839, Crowther, issued Sep. 17,1957; and U.S. Pat. No. 2,553,696, Wilson, issued May 21, 1951; allherein incorporated by reference.

Examples of modified polyamine cationic polymers of the presentinvention comprising PEI's, are illustrated in Formulas I-II;

Formula I depicts a polyamine cationic polymer comprising a PEI backbonewherein all substitutable nitrogens are modified by replacement ofhydrogen with a polyoxyalkyleneoxy unit, —(CH₂CH₂O)₇H, having theformula

This is an example of a polyamine cationic polymer that is fullymodified by one type of moiety.

Formula II depicts a polyamine cationic polymer comprising a PEIbackbone wherein all substitutable primary amine nitrogens are modifiedby replacement of hydrogen with a polyoxyalkyleneoxy unit, —(CH₂CH₂O)₇H,the molecule is then modified by subsequent oxidation of all oxidizableprimary and secondary nitrogens to N-oxides, said polyamine cationicpolymer having the formula

Another related polyamine cationic polymer comprises a PEI backbonewherein all backbone hydrogen atoms are substituted and some backboneamine units are quaternized. The substituents are polyoxyalkyleneoxyunits, —(CH₂CH₂O)₇H, or methyl groups. Yet another related polyaminecationic polymer comprises a PEI backbone wherein the backbone nitrogensare modified by substitution (i.e. by —(CH₂CH₂O)₇H or methyl),quaternized, oxidized to N-oxides or combinations thereof.

Of course, mixtures of any of the above described cationic polymers canbe employed, and the selection of individual polymers or of particularmixtures can be used to control the physical properties of thecompositions such as their viscosity and the stability of the aqueousdispersions.

In order to be most effective, the cationic polymers herein should be,at least to the level disclosed herein, in the continuous aqueous phase.In order to ensure that the polymers are in the continuous aqueousphase, they are preferably added at the very end of the process formaking the compositions. The fabric softener actives are normallypresent in the form of vesicles. After the vesicles have formed, andwhile the temperature is less than about 85° F., the polymers are added.

(K) Other Optional Ingredients

Silicones

The silicone herein can be either a polydimethyl siloxane (polydimethylsilicone or PDMS), or a derivative thereof, e.g., amino silicones,ethoxylated silicones, etc. The PDMS, is preferably one with a lowmolecular weight, e.g., one having a viscosity of from about 2 to about5000 cSt, preferably from about 5 to about 500 cSt, more preferably fromabout 25 to about 200 cSt Silicone emulsions can conveniently be used toprepare the compositions of the present invention. However, preferably,the silicone is one that is, at least initially, not emulsified. I.e.,the silicone should be emulsified in the composition itself. In theprocess of preparing the compositions, the silicone is preferably addedto the “water seat”, which comprises the water and, optionally, anyother ingredients that normally stay in the aqueous phase.

Low molecular weight PDMS is preferred for use in the fabric softenercompositions of this invention. The low molecular weight PDMS is easierto formulate without preemulsification.

Silicone derivatives such as amino-functional silicones, quatemizedsilicones, and silicone derivatives containing Si—OH, Si—H, and/or Si—Clbonds, can be used. However, these silicone derivatives are normallymore substantive to fabrics and can build up on fabrics after repeatedtreatments to actually cause a reduction in fabric absorbency.

When added to water, the fabric softener composition deposits thebiodegradable cationic fabric softening active on the fabric surface toprovide fabric softening effects. However, in a typical laundry process,using an automatic washer, cotton fabric water absorbency is appreciablyreduced when there is more than about 40 ppm, especially when there ismore than about 50 ppm, of the biodegradable cationic fabric softeningactive in the rinse water. The silicone improves the fabric waterabsorbency, especially for freshly treated fabrics, when used with thislevel of fabric softener without adversely affecting the fabricsoftening performance. The mechanism by which this improvement in waterabsorbency occurs is not understood, since the silicones are inherentlyhydrophobic. It is very surprising that there is any improvement inwater absorbency, rather than additional loss of water absorbency.

The amount of PDMS needed to provide a noticeable improvement in waterabsorbency is dependent on the initial rewettability performance, which,in turn, is dependent on the detergent type used in the wash. Effectiveamounts range from about 2 ppm to about 50 ppm in the rinse water,preferably from about 5 to about 20 ppm. The PDMS to softener activeratio is from about 2:100 to about 50:100, preferably from about 3:100to about 35:100, more preferably from about 4:100 to about 25:100. Asstated hereinbefore, this typically requires from about 0.2% to about20%, preferably from about 0.5% to about 10%, more preferably from about1% to about 5% silicone.

The PDMS also improves the ease of ironing in addition to improving therewettability characteristics of the fabrics. When the fabric carecomposition contains an optional soil release polymer, the amount ofPDMS deposited on cotton fabrics increases and PDMS improves soilrelease benefits on polyester fabrics. Also, the PDMS improves therinsing characteristics of the fabric care compositions by reducing thetendency of the compositions to foam during the rinse. Surprisingly,there is little, if any, reduction in the softening characteristics ofthe fabric care compositions as a result of the presence of therelatively large amounts of PDMS.

The present invention can include other optional componentsconventionally used in textile treatment compositions, for example:colorants; preservatives; surfactants; anti-shrinkage agents; fabriccrisping agents; spotting agents; germicides; fuigicides; anti-oxidantssuch as butylated hydroxy toluene; anti-corrosion agents; enzymes suchas proteases, cellulases, amylases, lipases, etc; and the like.

Particularly preferred ingredients include water soluble calcium and/ormagnesium compounds, which provide additional stability. The chloridesalts are preferred, but acetate, nitrate, etc. salts can be used. Thelevel of said calcium and/or magnesium salts is from 0% to about 2%,preferably from about 0.05% to about 0.5%, more preferably from about0.1% to about 0.25%.

The present invention can also include other compatible ingredients,including those as disclosed in copending applications Ser. No.:08/372,068, filed Jan. 12, 1995, Rusche, et al.; application Ser. No.08/372,490, filed Jan. 12, 1995, Shaw, et al.; and application Ser. No.08/277,558, filed Jul. 19, 1994, Hartman, et al., incorporated herein byreference.

Many synthesis methods can be used to prepare the principal solvents ofthis invention. Suitable methods are disclosed in the aforesaidcopending application, but should not be considered as limiting.

All parts, percentages, proportions, and ratios herein are by weightunless otherwise specified and all numerical values are approximaitonsbased upon normal confidence limits. All documents cited are, inrelevant part, incorporated herein by reference.

The following non-limiting Examples show clear, or translucent, productswith acceptable viscosities.

The compositions in the Examples below are made by first preparing anoil seat of softener active at ambient temperature. The softener activecan be heated, if necessary, to melting if the softener active is notfluid at room temperature. The softener active is mixed using an IKA RW25® mixer for about 2 to about 5 minutes at about 150 rpm. Separately,an acid/water seat is prepared by mixing the HCl with deionized (DI)water at ambient temperature. If the softener active and/or theprincipal solvent(s) are not fluid at room temperature and need to beheated, the acid/water seat should also be heated to a suitabletemperature, e.g., about 100° F. (about 38° C.) and maintaining saidtemperature with a water bath. The principal solvent(s) (melted atsuitable temperatures if their melting points are above roomtemperature) are added to the softener premix and said premix is mixedfor about 5 minutes. The acid/water seat is then added to the softenerpremix and mixed for about 20 to about 30 minutes or until thecomposition is clear and homogeneous. The composition is allowed to aircool to ambient temperature.

The following are suitable N,N-di(fatty acyl-amido)-N,N-dimethylammonium chloride fabric softening actives (FSA) with approximatedistributions of fatty acyl groups given, that are used hereinafter forpreparing the following compositions.

The following are suitable fabric softening actives (FSA) that are usedhereinafter for preparing the following compositions.

FSA¹: dioleyldimethylammonium chloride.

FSA²: di(canola)dimethylammonium chloride.

FSA³: diisostearyldimethylammonium chloride.

FSA⁴: 1-methyl-1-oleylamidoethyl-2-oleylimidazolinium methylsulfate(e.g., Varisoft® 3690).

FSA⁵: 1-methyl-1-(canola)amidoethyl-2-(canola)imidazoliniummethylsulfate.

FSA⁶: 1-oleylamidoethyl-2-oleylimidazoline.

FSA⁷: 1-(canola)amidoethyl-2-(canola)imidazoline.

FSA⁸: [R¹—C(O)—NH—CH₂CH₂—N(CH₃)(CH₂CH₂OH) —CH₂CH₂—NH—C(O)—R₁]⁺CH₃SO₄—wherein R₁—C(O) is oleoyl group (e.g., Varisoft® 222LT).

FSA⁹; [R₈—C(O)—NH—CH₂CH₂—N(CH₃) (CH₂CH₂OH)—CH₂CH₂—NH—C(O)—R₈]⁺CH₃SO₄—wherein R₈—C(O) is the (canola)alkyloyl group.

FSA¹⁰:

wherein R¹ is derived from oleic acid.

FSA¹¹; di(hydrocarbyl)dimethylammonium chloride, wherein the hydrocarbylgroup is derived from a mixture of oleic acid (fatty acid of FSA¹) andisostearic acid of FSA³ at an approximate 65:35 weight ratio.

FSA¹²; di(hydrocarbyl)dimethylammonium chloride, wherein the hydrocarbylgroup is derived from a mixture of canola fatty acid (fatty acid ofFSA²) and tallow fatty acid at an approximate 65:35 weight ratio.

FSA¹³: oleyltrimethylammonium chloride.

EXAMPLE I

1 2 3 4 5 6 7 8 Component Wt. % Wt. % Wt. % Wt. % Wt. % Wt. % Wt. % Wt.% FSA¹ 24 — — — — 9 9 — FSA² — 26.6 — — — — — — FSA³ — — 26.6 — — — — —FSA⁴ — — — 26.6 — — — — FSA⁵ — — — — 26.6 — — — FSA⁶ — — — — — 16.6 — —FSA¹³ 2.6 — — — — 1 1 — Ethanol 6 6 6 6 6 6 6 6 1,2-Hexanediol 17 17 1717 17 17 17 17 HCl (a) (a) (a) (a) (a) (a) (a) (a) Perfume 1.2 1.2 1.21.2 1.2 1.2 1.2 1.2 Kathon 3 ppm 3 ppm 3 ppm 3 ppm 3 ppm 3 ppm 3 ppm 3ppm DI Water Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. (a) To adjust pH ofthe Composition to about 3.5-4.0.

The above Examples show clear products with acceptable viscosities.

EXAMPLE II

1 2 3 4 5 6 7 8 Component Wt. % Wt. % Wt. % Wt. % Wt. % Wt. % Wt. % Wt.% FSA⁹ 26.6 — — — — — — — FSA¹⁰ — 26.6 — — — — — — FSA¹¹ — — 26.6 — — —— — FSA¹² — — — 26.6 — — — — FSA¹ — — — — 24 — — — FSA¹ — — — — — 24 — —FSA² — — — — — — 26.6 — FSA² — — — — — — — 26.6 FSA¹³ — — — — 2.6 2.6 —— Ethanol 6 6 6 6 6 6 6 6 1,2-Hexanediol 17 17 17 17 9.2 13 10 101,2-Pentanediol — — — — 6.8 2 — — 1,2-Octanediol — — — — — 1 — —2-Ethyl-1,3- — — — — — — 8 — Hexanediol 2,2,4- — — — — — — — 8Trimethyl- 1,3-pentanediol HCl (a) (a) (a) (a) (a) (a) (a) (a) Perfume1.2 1.2 1.2 1.2 1.2 1.2 1.2 1.2 Kathon 3 ppm 3 ppm 3 ppm 3 ppm 3 ppm 3ppm 3 ppm 3 ppm DI Water Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. (a) Toadjust pH of the Composition to about 3.5-4.0.

The above Examples show clear products with acceptable viscosities.

EXAMPLE III

1 2 3 4 5 6 7 8 Component Wt. % Wt. % Wt. % Wt. % Wt. % Wt. % Wt. % Wt.% FSA¹ — — — 9 39.3 14.8 — — FSA¹ — — — — — — — — FSA³ 26 — — — — — — —FSA⁴ — 26.6 — — — — — — FSA⁵ — — 27.5 — — — — — FSA⁶ — — — 16 — — — —FSA⁷ — — — — — 26.9 — FSA⁸ — — — — — — 45 — FSA⁹ — — — — — — — 43.2FSA¹³ — — — 1 3.9 1.5 — — 3-(Pentyloxy)- 18 — — — — — — —1,2-propanediol 1,2-bis — 18 — — — — — — (Hydroxy- methyl)cyclo- hexane1,2-Hexanediol — — 10 — 20 20 20 20 1,4-bis — — 8 — — — — — (Hydroxy-methyl)cyclo- hexane Hexylene- 6 6 4 6 10 4 6 10 Ethanol Isopropanol — —2 — — — 4 — HCl (a) (a) (a) (a) (a) (a) (a) (a) Perfume 1.2 1.2 1.2 1.21.2 1.2 1.2 1.2 Kathon 3 ppm 3 ppm 3 ppm 3 ppm 5 ppm 5 ppm 5 ppm 5 ppmDI Water Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. (a) To adjust pH of theComposition to about 3.5-4.0.

The above Examples show clear products with acceptable viscosities.

EXAMPLE VIII

Softeners on a 100% active basis Component (Wt %) 1 2 3 4 Varisoft-47526.0 — — — Varisoft-3690 — 26.0 — — Varisoft-222 LT — — 26.0 —Varisoft-222 LM — — — 26.0 Isopropanol 2.9 — 2.9 2.9 1,2-Hexanediol 20.020.0 20.0 17.0 HCl (1N) 0.25 0.25 0.25 0.25 Perfume 1.25 1.25 1.25 1.25DTPA 0.01 0.01 0.01 0.01 Kathon (1.5%) 0.02 0.02 0.02 0.02 DI Water49.57 52.47 49.57 52.57 Example: 1 2 3 4 IV (of starting fatty acid) 50105 105 50 Appearance (ambient) Opaque Clear Clear Cloudy Appearance(40° F.) Opaque Clear Clear Opaque Viscosity (cPs - ambient) 50 30 30 30Viscosity (cPs - 40° F.) 115 55 55 78

For commercial purposes, the above compositions are introduced intocontainers, specifically bottles, and more specifically clear bottles(although translucent bottles can be used), made from polypropylene(although glass, oriented polyethylene, etc., can be substituted), thebottle having a light blue tint to compensate for any yellow color thatis present, or that may develop during storage (although, for shorttimes, and perfectly clear products, clear containers with no tint, orother tints, can be used), and having an ultraviolet light absorber inthe bottle to minimize the effects of ultraviolet light on the materialsinside, especially the highly unsaturated actives (the absorbers canalso be on the surface). The overall effect of the clarity and thecontainer being to demonstrate the clarity of the compositions, thusassuring the consumer of the quality of the product.

What is claimed is:
 1. An aqueous, stable clear fabric softenercomposition containing: A. from about 2% to about 80% of fabric softeneractive containing at least two C₆-C₂₂ hydrocarbyl groups, but no morethan one being less than C₁₂ and the other is at least C₁₆, the groupshaving an IV from about 70 to about 140, or branched; and B. less thanabout 40% by weight of the composition of principal solvent having aClogP of from about 0.15 to about 0.64, and at least some degree ofasymmetry, said principal solvent containing insufficient amounts ofsolvents selected from the group consisting of:2,2,4-trimethyl-1,3-pentane diol; the ethoxylate, diethoxylate, ortriethoxylate derivatives of 2,2,4-trimethyl-1,3-pentane diol; and/or2-ethylhexyl-1,3-diol, to provide an aqueous stable composition bythemselves, said principal solvent being sufficient to make thecompositions clear.
 2. An article of manufacture comprising thecomposition of claim 1 in a clear bottle.
 3. The article of claim 2,wherein the bottle has a slight blue tint, sufficient to compensate forany light yellow color of the composition.
 4. The article of claim 2,wherein the bottle has an ultraviolet light absorber incorporated in thebottle wall to protect the composition.
 5. The composition of claim 1wherein said principal solvent B is present at an effective amount, butless than the amount required to achieve stability and the compositionis made stable by addition of another solvent that is itself inoperableto achieve stability.